Updated 6/27/2017 45th National Organic Chemistry Symposium 2017 – University of California, Davis

45th National Organic Chemistry Symposium Poster Sessions University of California, Davis The Robert and Margrit Mondavi Center for the Performing Arts

For each night’s poster sessions, prizes for the two best posters will be awarded. The Poster Awards are sponsored by the following ACS Journals:

Sunday: ACS Omega - Poster Awards will be presented Monday morning by Dean Tantillo, University of California, Davis Monday: Organic Letters – Poster Awards will be presented Tuesday morning by Sarah Reisman, California Institute of Technology Tuesday: The Journal of Organic Chemistry – Poster Awards will be presented Wednesday morning by Scott Miller, Yale University Wednesday: Organometallics – Poster Awards will be presented Thursday morning by Robert Bergman, University of California, Berkeley

Sunday, June 25, 2017 Poster # Poster Title Authors (*Presenting) Affiliation(s) An Investigation of Substituent Effects on S-1 Philip Albiniak* Ball State University the Electrophilicity of Oxypyridinium Salts

Juliet M. Alderson*, Jared W. Tunable, Selective Silver-Catalyzed Rigoli, Cale D. Weatherly, University of Wisconsin- S-2 Aminations and Oxidative Derivatization Alicia M. Phelps, Ryan J. Madison of Amines Scamp, Nicholas S. Dolan, Jennifer M. Schomaker

Preparation of Dienoic Acids as Rameez Ali*, Keveen Flieth, S-3 Intermediates in Syntheses of University of Nevada, Reno Thomas W. Bell Diterpenoids

†Universidad de Santiago Theoretical Study of Cu-Catalyzed C-H Iriux Almodovar*†, Edwin G. de Chile; ‡Pontificia S-4 Imidation of Benzaldehyde-oximes with Pérez Hernández‡, Carlos E. Universidad Católica de N-Fluorobenzenesulfonimide. Puerto Galvis# Chile; #Universidad Industrial de Santander

Synthesis and Evaluation of Martin Amezcua*; Ricardo California State University, S-5 Peptidomimetic Inhibitors for the Cruz; Nicholas Salzameda Fullerton Botulinum Neurotoxin

Synthesis of Isoquinoline Alkaloid Abigail K. Frndak, Karine E. S-6 Calvin College Derivatives Rose, Carolyn E. Anderson*

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Poster # Poster Title Authors (*Presenting) Affiliation(s) EPR Study of Catalyst Speciation, Off- Brittany Armstrong*, Richard Cycle Events, and Nonlinear Effects in an University of California, S-7 Sayler, Benjamin Shupe, R. Enantioselective Copper(II)-Catalyzed Davis David Britt, Annaliese K. Franz Spiroannulation

Enantioselective Total Synthesis of Lupin Viktor Barat*, Daniel Csokas, Nanyang Technological S-8 Alkaloids Roderick W. Bates University

Development of a Stereoselective and Kallol Basu*, Jeffrey T. Kuethe, S-9 Scalable Process for the Preparation of a Robert Orr, Eric Ashley, Marc Merck & Co. Methylcyclobutanol-Pyridyl Ether Poirer, Lushi Tan

Synthesis of Polycyclic Aromatic Marc R. Becker*, Corinna S-10 University of Michigan Hydrocarbons Schindler

Department of Chemistry Natural Products Isolation of Bioactive Jacquelyn Gervay-Hague, Amy S-11 University of California, Glycolipids in Tea, Camellia Sinensis Bellinghiere* Davis

Zoltán Benkő*, Larry Creemer, Joe Eckelbarger, Neeraj Sane, Tied Back Bispyridyloximes as Novel S-12 Carla Klittich, George Davis, Dow AgroSciences Agents for Crop Disease Control David Young, Stacy Meyer, Nick Wang

Metal-free C-H Sulfonamidation of Anna Berger*, Andreas U. University of Regensburg S-13 Pyrroles by Visible Light Photoredox Meyer, Burkhard König (Germany) Catalysis

Allison M. Bergmann*, Adam Advances in Copper-Catalyzed Cross- S-14 Oldham, Wei You, M. Kevin Indiana University Coupling Brown

Enantioselective Total Synthesis of Bijay Bhattarai*, Pavel S-15 Cannogenol and Cannogenol-3-O-alpha- University of Michigan Nagorny L-rhamnoside

Development of Strain-Releasing Florida Gulf Coast S-16 Methodologies Employing Gregory R. Boyce* University Cyclopropenones

A Novel Protocol for Synthesis of (Z)- Ronald Brisbois*, Scott Macalester College, S-17 10,11-dihydrobenzo[e][1,2,3]triazolo Pedersen, Hoang Anh Phan, St. Paul, MN [1,5- a]azocine Tia Eskridge, Claire Schmit

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Poster # Poster Title Authors (*Presenting) Affiliation(s) Diastereoselective Synthesis of Unnatural Molly Brown*, Natalie Dwulet, S-18 Amino Acids via an Auxiliary-directed Tina Zolfaghari, Daniel Occidental College Enolate Alkylation Essayan, Jeff Cannon

The Synthesis of New Precursors to Elise Brutschea*, Amadna S-19 Pentacyclo[4.3.0.02,4.03,8.05,7]non-4- Tallon, Linda Bui, Mark Saint Joseph's University ene Forman

Carlyn Reep, Shiyu Sun, Zhili Florida Institute of Helical-Chiral Pyridines for Catalytic S-20 Peng, Maurice Narcis, Norito Technology and University Transformations Takenaka* of Miami

Diastereoselective Tamura Cycloadditions Noah P. Burlow*, Sara Y. University of California, S-21 with N-Sulfonyl Ketimines Howard, Jared T. Shaw Davis

Dakota D. Butler*, Sarah N. Gold(I)-Catalyzed Synthesis of 1H- S-22 Cantu, Caitlin R. Lacker, Parker Southwestern University Isochromenes L. Wilson, Michael R. Gesinski

Highly Selective 5,5-Dimethyl-1,3,4,5- Xiao Cai*, Cristian Ramirez, tetrahydrobenz[cd]indole Synthesis by Anagu Tuoheti, Hassan Harb, University of California, S-23 Acid-Catalyzed Intramolecular Alkene Hrant P. Hratchian, Benjamin Merced Hydroarylation J. Stokes

The Influence of Oxidation State on the University of Michigan and Nicole M. Camasso*, Eric G. S-24 Selectivity of Bond-Forming Reactions at University of British Bowes, Melanie S. Sanford High-Valent Ni Complexes Columbia

Quantification of Alpha-gold Positive Robert G. Carden*, Nathan S-25 Charge Stabilization in Gold (I) Carbene Duke University Lam, Ross A. Widenhoefer Complexes

The Enantioselecive Synthesis of Mariel M. Cardenas*, Pyrrolopyrimidine Scaffolds through Christopher J. Nalbandian, S-26 San Diego State University Cation-Directed Nucleophilic Aromatic Sean T. Toenjes, Jeffrey L. Substitution Gustafson

Synthesis and in vivo Quantitation of 2’- Deoxyadenosine Adducts Resulting from Bioactivation of 4-(Methylnitrosamino)-1- Erik S. Carlson*, Pramod University of Minnesota - S-27 (3-pyridyl)-1-butanone and 4- Upadhyaya, Stephen S. Hecht Twin Cities (Methylnitrosamino)-1-(3-pyridyl)-1- butanol

S-28 Novel Synthesis of Isoflav-3-enes Maria G. Carranza* Westfield State University

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Poster # Poster Title Authors (*Presenting) Affiliation(s) Phosphonate-Directed Catalytic Suman Chakrabarty*, James University of Nebraska- S-29 Asymmetric Hydroboration: Synthesis of M. Takacs Lincoln Chiral Tertiary Boronic Esters

Dana Chambers*, Esmat Cobalt-Catalyzed C-O Bond Activation for University of California, S-30 Sodager, Raymond Sullivan, the Direct Functionalization of Alcohols Riverside Prof. Dave Martin

Wenyong Chen*, Peter Maligres, Feng Peng, John Process Development and Understanding Limanto, Artis Klapars, Jake Department of Process S-31 of Cyclization/Deprotection in the Song, Weidong Tong, Research and Synthesis of MK-3682 Guangtao Li, Timothy Nowak, Development, Merck Lin Wang, Meredith Green, Alfred Lee, Robert Dunn

†Division of Sustainable and Environmental Engineering, Graduate School of Engineering, Muroran Madhu Chennapuram*†, U.V. Institute of Technology, The Development of New Hybrid Type Subba Reddy†, Chigusa Seki†, Japan. ‡Tohoku Medical Squaramide Fused Amino Alcohol Yuko Okuyama‡, Eunsang and Pharmaceutical S-32 Organocatalysts and Its Application to Kwon#, Koji Kwai†, Michio University, Japan. Asymmetric Reactions Tokiwa§, Mitsuhiro Takeshita§, #Research and Analytical Hiroto Nakano† Center for Giant Molecules, Graduate School of Sciences, Tohoku University, Japan. §Tokiwakai Group, Japan

Process Optimization of a Late-Stage Alan H. Cherney*, Jason. S. S-33 Ring-Closing Metathesis (RCM) To Access Amgen Tedrow a 16-Membered Macrocycle

Synthesis of APEG-Derivative Surfactants Joseph Cheung*, Matthew S-34 for Study of Polybia-MP1 Structure and Roberson, Keveen Flieth, University of Nevada Reno Dynamics Matthew Tucker, Laina Geary

Study of the Behavior of (Z/E) 2- Judy M. Cifuentes*, John E. Pontificia Universidad S-35 Styrylbenzaldehyde O-Benzyloxime in Diaz, Alix E. Loaiza Javeriana Aza-6π Electrocyclization Reactions

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Poster # Poster Title Authors (*Presenting) Affiliation(s) James R. Hemmer, Saemi O. Department of Chemistry Poelma, Nicolas Treat, and Biochemistry and Zachariah A. Page, Neil D. Materials Department, Tunable Visible and Near Infrared Dolinski, Yvonne J. Diaz, Materials Research S-36 Photoswitches Warren Tomlinson, Kyle D Laboratory, University of Clark*, Joseph P. Hooper, California, Santa Barbara. Craig Hawker, Javier Read de Department of Physics, Alaniz Naval Postgraduate School

Cyclopentenone Formation via Remote Sarah E. Cleary*, Magenta J. S-37 University of Vermont C–H Insertion of Vinyl Cations Hensinger, Matthias Brewer

Synthesis of Vicinal Dichlorides via Alexander H. Cleveland*, S-38 Established Triphosgene-Pyridine Louisiana State University Rendy Kartika Protocol

Buchwald-Hartwig Amination of Soft Jacob W. Cleveland*, Jesse D. Tennessee Technological S-39 Lewis Basic Heterocyclic Complexant Carrick University Scaffolds

Lucas A. Zeoly, Lais, V. Acconcia, Rodrigo A. University of Campinas, Simple and Sustainable Approach to the S-40 Cormanich, Juan C. Paniagua, Department of Organic Synthesis of Pyrido-indolones Albert A. Moyano, Fernando Chemistry, Brazil Coelho*

University State of José Tiago Menezes Correia*, Catalytic Asymmetric Conjugate Addition Campinas, Max Planck S-41 Fernando Coelho, Benjamin of Indolizines to α,β-Unsaturated Ketones Institute für List Kohlenforschung

Brett Cory*, Giovanni G. University of California, Los Aqueous Dearomatization/Diels-Alder S-42 Castro, Michael E. Jung, David Angeles and Harvey Mudd Cascade for Teaching Labs A. Vosburg College

Extension of the Daphniphyllum Alkaloid Polycyclization Cascade to Joshua B. Cox*, Keita Komine, S-43 Baylor University Longeracemine’s Unprecedented Ring John L. Wood System

Heidi A. Dahlmann*, Amanda Organocatalyzed Intramolecular S-44 J. McKinney, Maria P. Santos, Berry College Carbonyl-Ene Reactions Lindsey O. Davis

Exploring the Scope of Lewis Acid- Mary Elisabeth Daub*, Hawa University of Wisconsin - S-45 catalyzed Triplet Energy Transfer: [2+2] Keita, Evan M. Sherbrook, Madison Photocycloaddition and Beyond Tehshik P. Yoon

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Poster # Poster Title Authors (*Presenting) Affiliation(s) Nucleophilic Dynamic Kinetic Resolution Sean Maddox, Gregory of Biaryl-Naphthoquinones Towards S-46 Dawson*, Nick Roschester, Dr. San Diego State University Functionally Diverse Atropisomeric Jeffrey Gustafson Scaffolds

Kimberly S. DeGlopper*, Expanding the Utility of the Nickel- Megan R. Kwiatkowski, Mason S-47 Mediated Decarbonylative Cross- Hope College C. Yoder, Trey C. Pankratz, Coupling of Substituted Phthalimides Jeffrey B. Johnson

Juan A. Vega, José Manuel Continuous Flow α-Arylation of Neuroscience Medicinal Alonso, Gabriela Méndez, S-48 N,N-Dialkylhydrazones Under Visible- Chemistry, Janssen Myriam Ciordia, Francisca Light Photoredox Catalysis Research & Development Delgado*, Andrés A. Trabanco

Heemal H. Dhanjee*, Yutaka Kobayashi, Jonas F. Buergler, Total Syntheses of (+) and (-) Travis C. McMahon, Matthew S-49 Baylor University Tetrapetalone A W. Haley, Jennifer M. Howell, Koichi Fujiwara, Lee Mains, John L. Wood

A Highly Convergent Total Synthesis of S-50 Dolabriferol C (One-pot Stereoselective Naveen Diddi*, Dale E. Ward University of Saskatchewan Bis-aldol Reactions)

Phosphorus NMR Probe to Quantify Hydrogen-bonding Ability of Silanols, Kayla M. Diemoz*, Annaliese University of California, S-51 Boronic Acids, and other Highly Utilized K. Franz Davis Organocatalysts.

An Atroposelective Dynamic Kinetic Andrew Dinh*, Ryan S-52 Resolution of Di-Aryl Ether San Diego State University Noorbehest, Jeffrey Gustafson Napthoquinones

Gihan Dissanayake*, Salim Modular Synthesis and Reactivity Javed, Dimuthu Vithanage, Department of Chemistry, S-53 Profiling Studies of Diverse C-, S-, and P- Arghya Ganguly, Paul R. University of Kansas based α,β-Unsaturated Macrocycles Hanson

Silicon 29 NMR Characterization of Per-O- Jacquelyn Gervay-Hague, University of California, S-54 Silylated Sugars Andras Domokos* Davis

Competition Studies with Host TETROL Department of Chemistry, and Four Cyclohexanone Guests: A Benita Barton, Sasha-Lee Nelson Mandela S-55 Sleuth’s Modus Operandi for Determining Dorfling*, Eric Hosten Metropolitan University, the Reasons for the Selectivity Order South Africa

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Poster # Poster Title Authors (*Presenting) Affiliation(s) Stanna K. Dorn*, Eric P. Rhodium-Catalyzed Intermolecular Weeda, Chad T. Compagner, S-56 Conversion of Ketones through C-C Bond Hope College Joseph M. Dennis, Jeffrey B. Activation Johnson

Preparation of Novel Hemi-1,2,4- Triazinyl-[2,2']-bypyridines via the Negishi Ryan P. Downs*, Ai-Lin Chin, Tennessee Technological S-57 Coupling and Telescoped Condensation Kayla M. Dean, Jesse Carrick University Towards Chemoselective Minor Actinide Separations

Scandium Catalyzed Substitution of Julia Duncan*, Lun Li, Laina S-58 University of Nevada, Reno Benzylic Alcohols Geary

A*STAR's Institute of Iron-Catalyzed Cross-Coupling Reactions Hung A. Duong*, Han Vinh Chemical and Engineering S-59 of Arylmagnesiums with Aryl Chlorides Huynh, Wenqin Wu, Qiaoqiao Sciences, Singapore; and Tosylates Teng, Yi-Yuan Chua National University of Singapore

Johannes B. Ernst*†, Christian Schwermann†, Fei Wang‡, N-Heterocyclic Carbenes – Powerful Gen-ichi Yokota‡, Mizuki †University of Münster and S-60 Ligands for Heterogeneous Catalysis Tada‡, Nikos L. Doltsinis†, ‡Nagoya University Satoshi Muratsugu‡, Frank Glorius†

Potentially Anticancer Peptides Related Nicholas A. Falcone*, Robin B. S-61 Hamilton College to Cryptomaldamide Kinnel

Copper-Catalyzed Approach to Beta- Gordon Farley*, Michael S-62 College of the Holy Cross Lactams Beauchamp, Andre K Isaacs

Phosphothreonine as a Catalytic Residue in Peptide-Mediated Asymmetric Baeyer- Aaron L. Featherston*, Scott J. S-63 Yale University Villiger Oxidations of Prochiral Miller Cyclobutanones

Total Synthesis of Leuconoxine by Radical Andrew J. Ferreira*, S-64 Oregon State University Translocation Christopher M. Beaudry

Laboratory of Organic Synthesis of Isocyanoacetates and Its Synthesis Bio and Reaction with Benzaldehyde. New Liliana Becerra-Figueroa*, S-65 Organocatalysis. Approach to the Synthesis 1,3- Diego Gamba-Sánchez Universidad de los Andes. Oxazepines. Bogotá-Colombia

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Poster # Poster Title Authors (*Presenting) Affiliation(s) Synthesis of Furanolactone Motifs using Jeffrey Cannon, Nicholas Foy, S-66 Photoredox/Lewis Acid-Catalyzed Ketyl Katherine Forbes*, Max Occidental College Radical Cyclizations Gruber

Jonathan R. Scheerer*, Matt Protective Natural Products from Grass- Nelli, Kelsey Miller, A.J. The College of William & S-67 Endophyte Associations Wright, M. Todd Hovey, Emily Mary Eklund, Margaret Olesen

Jiewei Jiang*, Alex M. Ayoub, Laura M.L. Hawk, Andrea J. Wisniewski, Neeraj K. Mishra, Ryan J. Herzig, Clifford T. Gee, Department of Medicinal Design and Synthesis of Peiliang Zhao, Jin-Yi Zhu, Chemistry and Institute for Dihydropyrimidine Analogs as BRFT S-68 Norbert Berndt, Thomas G. Therapeutics Discovery and Selective Inhibitors for Male Scott, Nana K. Offei-Addo, Jun Development, University of Contraception Qi, James E. Bradner, Ernst Minnesota Schönbrunn, Timothy R. Ward, William C.K. Pomerantz, Gunda I. Georg

Discovery of Selective Inhibitors and Xianghong Guan*, Zhenguan S-69 Fluorescence Tools for Testis-Specific Miao, Carolyn Kingsley, Jon University of Minnesota Bromodomain (BRDT) Hawkinson, Gunda I. Georg

Synthesis of Olefins via a One-pot Wittig Lun Li*, Jared C. Stimac, Laina S-70 University of Nevada, Reno Reaction and Catalytic Wittig Reaction M. Geary

Monday, June 26, 2017 Poster # Poster Title Authors (*Presenting) Affiliation(s) Expanding Diversity About the 3,4- R. Adam Mosey*, Christina Dihydroquinazoline Scaffold: Gaining Lake Superior State M-1 Magyar, Tyler Wall, Celina Access to an Emerging Class of University Malcolm, Martha Hutchens Antimicrobial Compounds

Synthesis of Highly Functionalized N- M-2 Carolyn E. Anderson* Calvin College Alkylated 2-Pyridones and Indolizines

Arghya Ganguly*, Salim Javed, Synthesis and Biological Evaluation of Gihan Dissanayake, Dimuthu M-3 Analogs of Lyngbouilloside and Sch- University of Kansas Vithanage, Berl R. Oakley, Paul 725674 R. Hanson

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Poster # Poster Title Authors (*Presenting) Affiliation(s) A Systematic Investigation of the Brooke Gantman*, Dominic Structure-Activity Relationships between M-4 McBrayer, Crissey Cameron, University of Nevada, Reno GBAP and the fsr Quorum Sensing Circuit Yftah Tal-Gan in Enterococcus faecalis

Structural Optimization of Atropisomeric Sean Toenjes, Valeria Garcia*, M-5 San Diego State University Pyrrolopyrimidine Structures Jeffrey Gustafson

Quantitation of Vapor Diffusions for Charles Garner*, Michael J. M-6 Baylor University Crystallization Wen

Hadi Gholami*, Aman Toward the Total synthesis of Kulshrestha, Kumar Dilip M-7 Michigan State University Salinosporamide A Ashtekar, Olivia K. Favor, Babak Borhan

Elizabeth L. Goldstein*, Progress Toward the Total Synthesis of California Institute of M-8 Hirokazu Takada, Brian M. Tylohirsuticine Technology Stoltz

Emilia J. Groso, Alexander N. Synthesis of 2,5-Dihydro-1H-pyrroles via Golonka*, Ryan A. Harding, University of Michigan, Ann M-9 Iron(III)-Catalyzed Carbonyl-Olefin Taylor M. Sodano, Corinna S. Arbor Metathesis. Schindler

Synthesis and Evaluation of Novel Erika Gotway*, Kaylan Calcium Channel Agonists with Kerrigan, Michael Frasso, M-10 University of Pittsburgh Applications in Lambert-Eaton Stephen Meriney, Man Wu, Myasthenic Syndrome Peter Wipf

Total Synthesis of Bioactive Phenolic Gennadii Grabovyi*, Justin University of Illinois at M-11 Natural Products Mohr Chicago

Rapid Asymmetric Synthesis of Steve Greszler*, Xenia Searle, M-12 ABBV/GLPG 2222, a Cystic Fibrosis Bhadra Shelat, Xueqing Wang, AbbVie, Inc. Corrector Clinical Candidate Eric Voight

Jacob Guerra*, Brandi Amide Bond Modulation: Cyclic Amines Mayson, Prarthana Kumar, California State University M-13 and Manipulating Energy Barriers Using Bhvandip Bajwa, V. V. Fresno DEET Analogs as a Model System Krishnan, Santanu Maitra

Copper-catalyzed Reductive Ireland- Siyuan Guo*, Kong-Ching The University of Hong M-14 Claisen Rearrangements for the Synthesis Wong, Pauline Chiu Kong of Allenoic Acids

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Poster # Poster Title Authors (*Presenting) Affiliation(s) Mechanism of Nakamura's Iron-Catalyzed Wes Lee, Jun Zhou, Lei Liu, University of Maryland M-15 Asymmetric Cross-Coupling Reaction: The Osvaldo Gutierrez* College Park Role of Spin in Controlling Selectivity

Functional Group Transformations of pi- M-16 Bonded Organic Compounds via Julia Gutsch*, John Gitua Drake University Epimetalation Process

One-Pot Synthesis of α-Carbonyl Bicyclic Khagendra Bahadur Hamal*, M-17 Furans via a Tandem Diels-Alder/5-Exo- University of Nevada, Reno Wesley A. Chalifoux Dig Cyclization/Oxidation Reaction

Backbone-Breaking Alkyl Shifts: A Christian S. Hamann*, Dean J. Albright College; University M-18 Common Theme in Sesquiterpene Tantillo of California, Davis Biosynthesis?

Structure-Activity Relationship Studies of Sally Hamry*, Chowdhury the Competence Stimulating Peptide Raihan Bikash, Yifang Yang, M-19 University of Nevada, Reno (CSP) Signal Utilized by Streptococci Bimal Koirala, Lucia Sanchez, Species Naiya Phillips, Yftah Tal-Gan

Jianxin Han*, Kelvin Yong, Safe, Selective Synthesis of a M-20 Antonio Ferretti, Nanfei Zou, Celgene Corporation Trifluoromethyl Pyrimidine Richard Heid, John Traverse

Climbing the Ladder of Complexity: Erin Hancock*, Nathan Line, M-21 Efforts Towards the Synthesis of Brittany Witherspoon, M. Indiana University Ladderane Natural Products Kevin Brown

Hiscotropic Rearrangements: Controlling Stephanie R. Hare*, Dean J. University of California, M-22 Product Outcomes for a Reaction with a Tantillo Davis Post-Transition State Bifurcation

Base-Controlled Linear or Branched Rh(I)- Gael Tran, Kevin Hesp*, Pfizer, Inc and Yale M-23 Catalyzed C-H ortho-Alkylation of Azines Vincent Mascitti, Jonathan University without Substrate Preactivation Ellman

Iridium-Catalyzed Stereoselective Allylic J. Caleb Hethcox*, Samantha California Institute of M-24 Alkylation Reactions with Crotyl Chloride E. Shockley, Brian M. Stoltz Technology

P. Badalov, K. Brak, A. Chtchemelinine, M. Frick, L Process Development of GS-5734, an Heumann*, B. Hoang, S. Process Chemistry, Gilead M-25 Antiviral Nucleotide Analog for the Neville, C. Regens, E. Rueden, Sciences, Inc., California Treatment of Ebola A. Stevens, A. Waltman, T. Vieira, L. Wolfe; B. Xu, J. Yu

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Poster # Poster Title Authors (*Presenting) Affiliation(s) Peyton M. Higgins*, Anisha Tyagi, Cindy Hu, Megan E. Isolation of Neurolenin D and Synthesis Neubig, Catherine McGeough, M-26 of Analogs for Treatment of Lymphatic Smith College Carter Kyle, Susan Mishiyev, Filariasis Steven A. Williams, Kevin M. Shea

Concise Total Synthesis of Kirill Popov, Anita Hoang*, M-27 Lund University Dehaloperophoramidine Peter Somfai

Julie L. Hofstra*, Naoyuki Nickel-Catalyzed Asymmetric Reductive Suzuki, Kelsey E. Poremba, California Institute of M-28 Cross-Couplings with Vinyl Bromide Alan H. Cherney, Sarah E. Technology Electrophiles Reisman

A Sequential Cycloaddition Strategy for Allen Y. Hong*, Christopher D. University of California, M-29 the Total Synthesis of Alsmaphorazine B Vanderwal Irvine and Related Alkaloids

Andreas Baur, Lijun Chen, Rob Oxidative Decarboxylative Coupling A. Crovak, Aaron P. Honeycutt, M-30 Reactions: Development and Mechanistic West Virginia University Lin Ju, Minghao Li, Jessica M. Insights Hoover*

Combining Copper-Catalyzed Pedro A. Horn*, Roger K. Hydroboration with Palladium-Catalyzed Braun, Victória G. Isoppo, Federal University of Rio M-31 Suzuki Coupling for the One-pot Synthesis Jessie S. da Costa, Diogo S. Grande do Sul, Brazil of Arylallylamines under Micellar Ludtke, Angélica V. Moro Conditions

Matthew A. Horwitz*, Naoya Tanaka, Takuya Yokosaka, Blane P. Zavesky, Jesus I. Advances in Stereoselective Umpolung Martinez-Alvarado, Jessica A. and Aldol Reactions and Progress University of North M-32 Griswold, Leslie V. Leiva, Dr. Towards the Total Synthesis of Three Carolina at Chapel Hill Elisabetta Massolo, Prof. Dr. Veratrum Alkaloids Daisuke Uraguchi, Prof. Dr. Takashi Ooi, Prof. Dr. Jeffrey S. Johnson

Department of Chemistry, Enantiospecific Total Synthesis of the The Scripps Research M-33 Highly Strained (−)-Presilphiperfolan-8-ol Pengfei Hu*, Scott A. Snyder Institute and Department via a Pd-Catalyzed Tandem Cyclization of Chemistry, University of Chicago

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Poster # Poster Title Authors (*Presenting) Affiliation(s) Kuan-Hsun Huang*, Chia-Yu Hsu, Tai-Yu Chiu, Yu-Wei Liu, Institute of Biotechnology Function-Oriented Synthesis of Yun-Yu Chen, Teng-Kuang Yeh, and Pharmaceutical M-34 Phosphatidylserine Targeting Drug Jiing-Jyh Jan, Yu-Chen Huang, Research, National Health Conjugate via Click Chemistry Chen-Lung Huang, Ming-Yu Research Institutes Fang, Tsu-An Hsu, Chiung- Tong Chen, Lun K. Tsou

The Unexpected Degradation Pathways of Daclatasvir, an Imidazole Derivative, Bristol-Myers Squibb M-35 Yande Huang*, Scott A. Miller under Forced Photo-Oxidative Company Degradation Condition

Brandi M. Hudson*, Gydo van Automated Modeling of Alternative Zundert, Daniel Keedy, University of California, San M-36 Ligand Conformations in Protein Crystal Kenneth Borrelli, Tyler Day, Francisco; Schrödinger Structures for Structure-Based Design James Fraser, Henry van den Bedem

(5,6-Dihydro-1,4-dithiin-2-yl)methanol as Jan Hullaert*, Mien M-37 a Versatile Allyl-Cation Equivalent in (3+2) Ghent University Christiaens, Johan M. Winne Cycloaddition Reactions

Pushing the Limit on Regioselective David Hurem*, David McLeod, Deprotonation of Trialkylphosphine- M-38 Arkesh Narayanappa, James McMaster University Derived Phosphonium Salts Directed by McNulty Cyclic Acetal Protecting Groups

Ring Expansion of Cyclic Peptide Jing Shang, Carlie L. Charron, M-39 University of Melbourne Thioamides Craig A. Hutton*

Formation, Alkylation and Hydrolysis of Uyen Huynh*, Daniel Lim, Chiral Nonracemic N-Amino Cyclic Sarah E. Wengryniuk, Stacey L. M-40 Carbamate Hydrazones: An Effective University of Houston McDonald, Md. Nasir Uddin, Approach to the Enantioselective α- Sumit Dey, Don M. Coltart Alkylation of Ketones

André K Isaacs*, Aaron Bosse, Copper-Catalyzed Approach to Beta- M-41 Christopher DeTroia, Gregory College of the Holy Cross Gamma Unsaturated Amides Tsougranis

Peripheral Modifications of [Ψ[CH NH]Tpg4]Vancomycin with Added Akinori Okano, Nicholas A. The Scripps Research M-42 2 Synergistic Mechanisms of Action Provide Isley*, Dale L. Boger Institute Durable and Potent Antibiotics

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Poster # Poster Title Authors (*Presenting) Affiliation(s) An Intriguing Concentration-dependent Jake Ravi Jagannathan*, Kayla University of California, M-43 Catalyst Order for a Siloxanol-catalyzed Diemoz, Annaliese Franz Davis Conjugate Addition Reaction

Rhodium-Catalyzed Enantioselective Youngjin Jang*, Egor. M. Larin, M-44 Reductive Arylation: Convenient Access University of Toronto Mark Lautens to 3,3-Disubstituted Oxindoles

A La(OTf)3-catalyzed Multi-component Julia J. Jennings*, Alayna H. Reaction for the Synthesis of Nguyen, Blanca I. Gomez, University of California, M-45 Malonamides and a Quantitative Binding Benjamin W. Wigman, Davis Study of Lewis Acid Catalysts Annaliese K. Franz

An Intramolecular para-Phenolic Allylation Free Radical Cyclization Nicholas Jentsch*, Matthew University of Southern M-46 Strategy for the Synthesis of Alkaloids Donahue Mississippi and Terpenes with Spiro[4.5]decane Architectures

Stereodivergent Allylic Substitutions with Xingyu Jiang*, Jason J. Beiger, Univesity of California, M-47 Aryl Acetic Acid Esters by Synergistic John F. Hartwig Berkeley Iridium and Lewis Base Catalysis

John Johnson*†, Chelsea Soward†, John Hammer†, †Northern Kentucky M-48 Phenylethynyl Oxacalixarenes Bethany Pertzsch†, Kristin University, ‡Colby College, Esdale‡, Jeff Katz‡, KC Russell†

Department of Chemistry, Synthesis and Biological Application of Dylan E. Jones*, Victor Van University of Nevada, Reno, Small Molecules to Investigate the Puyenbroeck, Kurt Vermeire, Rega Institute for Medical M-49 Mechanism of Action of the Signal Dominique Schols, Thomas W. Research, Katholieke Sequence Specific Small Molecule Bell Universiteit Leuven, Cylcotriazadisulfonamide Belgium

Development of Cu(II) Detection Probes M-50 and their Application to Pharmaceutical Jiyoung Jung* Penn State University Compounds

Approach to the Total Synthesis of Jessica Jünger*, Rathikrishnan Eberhard-Karls University M-51 Gulmirecin A and B Rengarasu, Martin E. Maier of Tübingen

Total Synthesis of Juglorubin, A Natural Shogo Kamo*, Kai Yoshioka, Kyoto Prefectural M-52 Red Dye Containing a Cyclopentadienyl Kouji Kuramochi, Kazunori University, Tokyo Anion Tsubaki University of Science

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Poster # Poster Title Authors (*Presenting) Affiliation(s) Progress Toward the Total Synthesis of Alexander S. Karns*, University of California M-53 Kalihinol A Christopher D. Vanderwal Irvine

The Syntheses of (+)-Zincophorin Methyl Zachary A. Kasun*, Hiroki Ester and Nanographenes: Natural and Sato, Yasuyuki Mori, Jing Nie, The University of Texas at M-54 Unnatural Products through C-C Bond Xin Gao, Radoslaw Lipinski, Austin Forming Transfer Hydrogenation Michael J. Krische

Toward Solid State Proton Conduction: Reuben Hudson, Ramesh Y. Evaluation of Carboxylic, Phosphonic and Colby College and Adhikari, Mark T. Tuominen, S. M-55 Sulfonic Acid Protogenic Moieties on University of Thayumanavan, Jeffrey L. Tunable Poly(meta-phenylene oxide) Massachusetts Amherst Katz* Scaffolds

Riley H. Kaufman*, Justin Expanded Scope of Oxidopyrylium-Alkene Simanis, C. Marshall Law, Erica M-56 [5+2] Cycloaddition Conjugate Addition Illinois State University L. Woodall, John R. Goodell, T. Cascades Andrew Mitchell

Synthesis of Cyclopalladated Department of Chemistry, Azobenzenes Coordinated to N- Amanpreet Kaur*, Tarlok S. Guru Nanak Dev University, Substituted Imidazolidine-2-thione and M-57 Lobana, Geeta Hundal, Jerry P. India and Department of Allied Ligands: Molecular Structures, Jasinski Chemistry, Keene State Spectroscopy, Fluorescence and ESI- College, New Hampshire Mass Studies

γ-Functionalization of Enones via Silyl Nabeelah I. Kauser*, Xiaohong University of Illinois at M-58 Dienol Ethers Chen, Justin T. Mohr Chicago

Synthesis of [2.2.2]-Diazabicyclic Jonathan Perkins*, Xiye The College of William and M-59 Alkaloids Wang*, Dr. Jonathan Scheerer Mary

Chemoselective Copper-Catalyzed Sean M. Kelly*, Chong Han, M-60 Ullmann-Type Coupling of Oxazolidinones Genentech, Inc. Laura Tung, Francis Gosselin with Bromoiodoarenes

Advances in Regioselective Additions to Hilary A Kerchner*, John M-61 University of Michigan pi Systems Montgomery

Pincer-Ligated Ir(III) Complexes for Kelly E. Kim*, Karen I. M-62 University of Washington Alkane Dehydrogenation Goldberg

The Total Syntheses of Aromathecin-, Protoberberine- and Tylophora Alkaloids Tobias Knecht*, Andreas M-63 Enabled by an Cp*Co(III)-Catalyzed Lerchen, Maximilian Koy, University of Muenster Intramolecular C–H Activation/Cyclization Frank Glorius Reaction

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Poster # Poster Title Authors (*Presenting) Affiliation(s) Isomerization of Olefins Using Pd(II) Andrew L Kocen*, Maurice M-64 University of Houston Catalysts Brookhart, Olafs Daugulis

Kavoos Kolahdouzan*†, O. †Pomona College and Probing the Equilibrium Isotope Effects in M-65 Maduka Ogba†, Annaliese K. ‡University of California, 1,3-Disiloxanediols Franz‡, Daniel J. O'Leary† Davis

Synthesis of trans-Cinnamyl Ester Andrew B. Lutjen, Mackenzie M-66 Derivatives via a Greener Steglich A. Quirk, Allycia M. Barbera, Siena College Esterification Erin M. Kolonko*

Synthesis and Optimization of ClpXP- Vadim S. Korotkov*, Christian Technische Universität M-67 Inhibitors Fetzer, Stephan A. Sieber München

Kevin M. Kossick*, Taeboem California State University, M-68 N,N-Diarylbenzimidazolium Compounds Oh Northridge

Synthesis and Critical Evaluation of Daniel Kovacs*, Xi Lu, Lívia S. M-69 Coumarin and Carbostyril-sensitized Mészáros, Marjam Ott, Julien Uppsala University Luminescent Lanthanide Complexes Andres, K. Eszter Borbas

Cascade Reactions of Nitrones and Michelle A. Kroc*, Wiktoria H. Allenes – Asymmetic Synthesis of University of Illinois at M-70 Pace, Tyler W. Reidl, Dong- Dihydropyridoindoles and Preparation of Chicago Liang Mo, Laura L. Anderson Functionalized Indoles

Michael R. Krout*, Brandon N. Stereoselective Synthesis of the Allo Bile M-71 Nelson, Samantha P. Kelly, Bucknell University Acids Brett J. Huckstep

Kouji Kuramochi*, Shoma Biomimetic Syntheses of (±)- Tokyo University of Science Mizutani, Kenta Komori, M-72 Rubrobramide, (±)-Flavipucine, and Kyoto Prefectural Chiharu Kai, Yasuha Kusakabe, Isoflavipucine, and (±)-Berkeleyamide D University Kazunori Tsubaki

Synthesis of Gyramide-Bound Ada J. Kwong*, Thiago Santos, University of California, M-73 Photoaffinity Reagents and Analogs for Lucas C. Moore, Douglas Davis and University of DNA Gyrase Inhibition Weibel, Jared T. Shaw Wisconsin-Madison

Scott Savage*, Theresa Fast Track Process Research: Cravillion, Ngiap-Kie Lim, Process Chemistry, M-74 Identification and Development of Highly Andrew McClory, Haiming Genentech Inc. Improved Routes to GDC-0810 Zhang, Chong Han, Francis Gosselin

N. Warner*, M. Zhao, D. Pomona College and M-75 ROMP for Pulmonary Antibiotic Delivery Ratner, L. Chery, D. O’Leary University of Washington

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Updated 6/27/2017 45th National Organic Chemistry Symposium 2017 – University of California, Davis

Tuesday, June 27, 2017 Poster # Poster Title Authors (*Presenting) Affiliation(s) Cu+ Interrupts the Concerted Cope Croix J. Laconsay*, Dibyendu The Hebrew University of T-1 Rearrangement of Semibullvalene Mallick, Sason Shaik Jerusalem

Exploring New Methodologies for the Andrew R. LaDuca*, Thomas Dept. of Chemistry, Grand T-2 Treatment of Nuclear Waste using Neils, John E. Bender, Valley State University, Ligands Containing Soft Donors Shannon M. Biros Michigan

Asymmetric Rhodium-Catalyzed Summer D. Laffoon*, Kami L. University of Illinois at T-3 Synthesis of Chiral β-Branched Esters Hull Urbana-Champaign

William T. Lambert*, Miriam Synthesis and Evaluation of Insecticidal Dow AgroSciences, Kelly T-4 E. Goldsmith, Thomas C. Thioureas and Isothioureas Services Sparks

Development of Ester-Protected Ethambutol Derivatives for Erik Larsen*, Dominique T-6 Butler University Characterization of Mycobacterial Stephens, R. Jeremy Johnson Hydrolase Activity

Stephen W. Laws*, Lucas C. Catalytic Formal [4+2] Reactions of Moore*, Michael J. Di Maso, University of California, T-7 Imines and Cyclic Anhydrides for the Nhu N. Nguyen, Dean J. Davis Stereoselective Synthesis of Lactams Tantillo, Jared T. Shaw

Thanh-Ngoc Le*, Steven P. Mechanistic Evaluation of Diboron(II,II)- Cummings, Jose Alvarenga*, University of California, T-8 Mediated Pd-Catalyzed H Atom Transfer Alberto R. Navarro Brito, Merced From Water Hassan Harb, Hrant P. Hratchian, Benjamin J. Stokes

University of Nevada, Reno Synthesis of Cyclotriazadisulfonamide Truc D. Le*, Dominique Schols, and the Rega Institute for T-9 Analogues Towards the Down- Kurt Vermeire, Thomas W. Medical Research, modulation of CD4. Bell Katholieke Universiteit Leuven

Nathan N. Le*, Aimee M. Titanium-mediated Synthesis of Rodriguez, Jillian M. Bradley, T-10 Southwestern University Cyclobutane Derivatives Renee E. Walker, James R. Alleyn, Michael R. Gesinski

Korea Advanced Institute T-11 Total Synthesis of (±)-Waihoensene Hongsoo Lee*, Hee-Yoon Lee of Science and Technology

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Poster # Poster Title Authors (*Presenting) Affiliation(s) Internal Oxidizing Directing Groups: A Andreas Lerchen*, Tobias Toolkit in C-H Activation for the Efficient Knecht, Suhelen Vásquez- T-12 University of Muenster Construction of Valuable Target Céspedes, Constantin G. Molecules Daniliuc, Frank Glorius

Joyce Leung*, Aaron Bedermann, Naoto Hama, Synthetic Studies Toward the Total T-13 Graham Murphy, Christopher Baylor University Synthesis of Phomoidride D Schneider, Ping Dong, John L. Wood

Department of Physiology & Pharmacology - Program in Chemical Biology, Synthesis of Fluorogenic Probes to Detect Samantha R. Levine*, Katie R. Department of Biomedical T-14 Esterase Activity in Mycobacterium Tallman, Kimberly E. Beatty Engineering, OHSU Center tuberculosis for Spatial Systems Biomedicine, Oregon Health & Science University

Palladium-NOx Mediated Aerobic Jiaming Li*, Brian M. Stoltz, California Institute of T-15 Intramolecular Aminoacetoxylation of Robert H. Grubbs Technology Alkenes

Catalytic Alkylation of Quinones via T-16 Xiao-Long Xu, Zhi Li* ShanghaiTech University Redox Chain Reaction

Highly Regioselective Hydrochlorination Shengzong Liang*, Rene T-17 of Alkynes with a Novel Chlorinating Ebule, Bo Xu, Gerald B. University of Louisville Reagent Hammond.

Chris Limberakis*†, Markus Boehm†, Rushia Turner‡, †Pfizer, ‡University of Synthesis and Membrane Permeability Siegfried S. F. Leung#, Guoyon California, Santa Cruz, and T-18 Assessment of Novel Cyclic Peptide- Bai†, Gilles H. Goetz†, David A. #University of California, Peptoid Hybrids Price†, Spiros Liras†, Alan M. San Francisco Mathiowetz†, Matthew P. Jacobson#, R. Scott Lokey‡

Zhuqing Liu*, Alan Hyde, Artis Klapars, John Chung, George Efficient Synthesis of MK-8666 Using Merck Research T-19 Zhou, Zhijian Liu, Nobuyoshi Highly Regioselective Michael Addition Laboratories Yasuda, John Limanto, Kevin Campos, Benjamin D. Sherry

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Poster # Poster Title Authors (*Presenting) Affiliation(s) Xinyun Liu*, Ben Haugeberg, Quinone-catalyzed Oxidative T-20 Johnny Phan, Shrikant Londhe, University of Kansas Functionalization of Amines Michael Clift

Department of Chemistry and Biochemistry, and Visible-light Promoted C-S Bonds Bin Liu*, Chern-Hooi Lim, Materials Science and T-21 Formation via Intermolecular Charge- Garret M. Miyakea Engineering Program, transfer University of Colorado Boulder

Synthesis and Applications of Moriah Locklear*, Patrick University of Nebraska T-22 Trifluoromethyl Peroxides Dussault Lincoln

Kaitlyn M. Logan*, Kevin B. T-23 Stereoselective Alkene Carboboration Indiana University Smith, M. Kevin Brown

Synthesis of Benzodihydropyranic Structures as 2H-Chromenes Precursors Alvaro Rodríguez-López*, Universidad de los Andes T-24 Using an Intramolecular Pummerer Diego Gamba-Sánchez (Colombia) Reaction

Jacob R. Ludwig*, Christopher A. McAtee, Paul S. Riehl, Haley Iron-Catalyzed Carbonyl-Olefin T-25 Albright, Emilia J. Groso, Ryan University of Michigan Metathesis A. Harding, Alexander N. Golonka, Corinna S. Schindler

†Department of Chemistry, University of Nevada, Reno Synthesis of Pyridine-fused Liezel A. Lumangtad*†, and ‡Rega Institute for T-26 Cyclotriazadisulfonamides and Bicyclam Thomas W. Bell†, Dominique Medical Research, KU Analogs as HIV Entry Inhibitors Schols‡, Kurt Vermeire‡ Leuven, University of Leuven

PhI-Catalyzed α-Tosyloxylation of Wuping Ma*†, Richard Ma‡, †SynChem, Inc. and ‡Lake T-27 Cyclopropyl Methyl Ketone Daniel Fang† Forest High School

A Nucleophilic Dynamic Kinetic Sean M. Maddox*, Gregory, A. T-28 Resolution of Aryl-Naphthoquinone San Diego State University Dawson, Jeffrey L. Gustafson Atropisomers

Gabriel Magallanes*, Irene Catalysis Facilitates Fragmentation of Bosque-Martinez, Mathilde T-29 University of Michigan Lignin Rigoulet, Markus D. Kärkäs, Corey R. J. Stephenson

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Poster # Poster Title Authors (*Presenting) Affiliation(s) Joshua A. Malone*, Joshua P. Silyloxyallyl Cation: Synthesis of Van Houten, Moshood O. T-30 Functionalized 1,4-Diketones and Louisiana State University Ganiu, Binod Nepal, Rendy G. Substituted Pyrroles Kartika

5-Acyl-5-phenyl-1,5-dihydro-4H-pyrazol- 4-ones − Highly Selective Acylating Kostiantyn O. Marichev*, University of Texas at San T-31 Reagents for Polyamines and Michael P. Doyle Antonio Aminoglycosides

Cu-catalyzed γ-alkylation of Enones and Jenny S. Martinez*, Hamza University of Illinois at T-32 γ-hydroxylation of Vinylogous Esters Saifuddin, Justin T. Mohr Chicago

The Asymmetric Synthesis of Thujone via Kellie M. Martinez*, Gregory Florida Gulf Coast T-33 a Cycloisomerization Strategy R. Boyce University

Total Synthesis of (+)-Callyspongiolide: An Max-Planck-Institut für Guillaume Mata*, Alois T-34 Exercise for Ring Closing Metathesis of Kohlenforschung, Mülheim Fürstner Terminal Alkyne an der Ruhr, Germany

Desymmetrization of Fused Heterocycles Desiree M. Matias*, Jeffrey S. University of North T-35 Derived from Benzene Oxide to Access Johnson Carolina at Chapel Hill Highly Substituted Cyclohexanes

A Mechanistic Examination of the Christina H. McCulley*, University of California, Influence of Alkene Substitution on Rates Michael J. Geier, Brandi M. Davis and University of T-36 of Biomimetic Platinum-Promoted Hudson, Michel R. Gagne, North Carolina at Chapel Polyene Polycyclizations Dean J. Tantillo Hill

Direct C−H Cyanation of Arenes via Joshua B. McManus*, David A. University of North T-37 Organic Photoredox Catalysis Nicewicz Carolina at Chapel Hill

Lea-Marina Mehl*, Martin E. T-38 Total Synthesis of Lingzhiol University of Tübingen Maier

Kelsey M. Mesa*, Hailey A. NaBArF Catalyzed Michael Addition University of California, T-39 Hibbard, Sean O. Wilson, Reactions and Mechanistic Studies Davis Annaliese K. Franz

Insertion of Aryne into T-40 Milad Mesgar*, Olafs Daugulis University of Houston Bis(trifluoromethyl)disulfide

Synthesis and Biological Investigations of Sharon E. Michalak*, Zef A. University of California, T-41 the Haterumaimide and Lissoclimide Könst, Chris D. Vanderwal Irvine Natural Products

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Poster # Poster Title Authors (*Presenting) Affiliation(s) Metallacycle-mediated Annulative Cross- Haruki Mizoguchi*, Glenn C. Department of Chemistry, T-42 coupling for the Synthesis of Angularly- Micalizio Dartmouth College Substituted Stereodefined Decalins

N O as a Promoter of the Pauson-Khand Vahid Mohammadrezaei*, T-43 2 University of Nevada, Reno Reaction David Ricker, Laina M. Geary

Derek Morrelli*, Jacob Guerra, Solvent Effects on Rotational Energy Prarthana Kumar, Bhvandip California State University, T-44 Barriers in Cyclic Amine DEET Analogs Bajwa, V. V. Krishnan, Santanu Fresno Maitra

Seann P. Mulcahy*, Michael A. O'Donnell, Satyam Khanal, Cyclization Reactions of Alkynamides and T-45 Sean P. Wrenn, Junho Song, Providence College Cyanamides Kathryn E. Queenan, Jonathan G. Varelas

Mina C. Nakhla*, John L. T-46 Synthetic Studies Toward Aspergilline A Baylor University Wood

Daniel J. Nasrallah*, Jacob R. Interrupted Carbonyl-olefin Metathesis Ludwig, Rebecca B. Watson, T-47 University of Michigan Reaction Dr. Joseph B. Gianino, Dr. Corinna S. Schindler

One-pot Sequential Strategies for the Cornelius N. Ndi*, Paul R. T-48 Synthesis of Polyol Fragments: University of Kansas Hanson Applications in Natural Product Synthesis

Cobalt-Catalyzed C-H Functionalization of T-49 Tung Nguyen*, Olafs Daugulis University of Houston Carboxylic Acids

Gesine K. Veits, Gabrielle Hammersley, Meghan F. Advancements Towards the Aza- University of California, T-50 Nichol*, Helena C. Steffens, Piancatelli Rearrangement Santa Barbara Ember L. Doherty, Javier Read de Alaniz

Scott Niman*, Isaac Wang, T-51 Total Synthesis of DAB-1 Occidental College Alex Rand, Jeffrey Cannon

Terdockin - Predicting Binding Modes of Terrence E. O'Brien*, Steven J. University of California, T-52 Cationic Intermediates for Terpene Bertolani, Justin B. Siegel, Davis Synthases Dean J. Tantillo

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Poster # Poster Title Authors (*Presenting) Affiliation(s) Microwave-assisted Gold(I)-catalyzed James V. Oakley*, Tyler California State University T-53 Friedel-Crafts-like Arylation of Benzylic Stanley, Stephanie E. Cain, San Marcos Alcohols to Afford 1,1-Diarylmethanes Robert G. Iafe

Douglas L. Orsi*, Brandon J. The University of Kansas, Base Catalysis Enables Access to α,α- T-54 Easley, Jacob P. Sorrentino, Department of Medicinal Difluoroalkyl(thio)ethers Ashley M. Lick, Ryan A. Altman Chemistry

Amy A. Ott*, Charles S. T-55 The SAD DKR of Symmetric Allylic Azides University of Minnesota Goshey, Joseph J. Topczewski

Ryan D. Otte*, J. Michael Ellis, Michael Altman, Neville J. Anthony, John W. Butcher, Brandon Cash, Matthew Syk Inhibitor Evolution: Rational Design Christopher, Danielle Falcone, Merck Research T-56 and Serendipitous Discovery of Kinome Andrew M. Haidle, James Laboratories Selective Chemotypes Jewell, Matthew Maddess, Kerrie Spencer, Binyuan Sun, Dilrukshi Vitharana, Youwei Yan, Hua Zhou, Hani Houshya, Alan B. Northrup

Mary H. Packard*, James H. The Effect of Proximal Functionality on T-57 Cox, Victoria P. Suding, Joseph University of Minnesota the Allylic Azide Rearrangement J. Topczewski

Copper-catalyzed Enaminone Synthesis T-58 Using Donor/Acceptor Substituted Diazo Arpan Pal*, Syed R. Hussaini The University of Tulsa Compounds

Zara Parkinson*, Zain Virk, Anoushka Mullasseril, Dr. Synthesis of Peptides Modeling Domains T-59 Kimberly Brien, Dr. Roberto de Rhodes College on PLA2R la Salud Bea, Dr. Shana Stoddard

Manee Patanapongpibul*, Optimization of Diarylpentadienones as California State University, T-60 Guanglin Chen, XiaoJie Zhang, Chemotherapeutics for Prostate Cancer Fresno Qiao-Hong Chen

Computational Design, Synthesis and Ryan M. Pearson*, Garret M. University of Colorado T-61 Application of Highly Reducing Organic Miyake Boulder Photocatalysts

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Updated 6/27/2017 45th National Organic Chemistry Symposium 2017 – University of California, Davis

Poster # Poster Title Authors (*Presenting) Affiliation(s) Syntheses of Stable Isotope-labeled Precursors for Probing Biosynthetic Q. Huy To, M. Soledade C. T-62 University of Saskatchewan Pathways of the Cruciferous Phytoalexins Pedras* Nasturlexins

Escuela de Química, Universidad Industrial de Synthesis of Amidoximes by Copper- Santander, Bucaramanga, T-63 catalyzed Coupling of Aldoximes and Carlos Bueno, Edwin G. Pérez* Colombia and Department Nitrogen Radicals of Organic Chemistry, Pontifical Catholic University, Santiago, Chile.

Discrimination Between o-Xylene, m- Xylene, p-Xylene and Ethylbenzene by Benita Barton, Eric C. Hosten, Nelson Mandela T-64 Host Compound (R,R)-(–)-2,3-Dimethoxy- Pieter Pohl* Metropolitan University 1,1,4,4-tetraphenylbutane-1,4-diol

Matthew R. Porter*, Rami M. Allylic Azide Resolution by Friedel-Crafts T-65 Shaker, Cristian Calcanas, University of Minnesota Alkylation Joseph J. Topczewski

Scope and Optimization of the Double Knorr Cyclization: On Route to Novel 1,8- T-66 Allan M. Prior*, Dianqing Sun University of Hawaii at Hilo Diazaanthraquinones as Potential Antituberculosis Agents

Nicholas Wong*, Xin Linghu, Hans Iding, Vera Jost, Stefan Process Development of ERK Inhibitor T-68 G. Koenig, Haiming Zhang, C. Genentech Inc. GDC-0994 Gregory Sowell, Francis Gosselin

Vaneet Saini*, Richard Novartis Institute for Development and Mechanistic Insight Thornbury, Talita de BioMedical Research; T-69 into a Palladium-Catalyzed Fernandes, Celine Santiago, University of California, Arylfluorination Reaction of Chromenes Eric Talbot, Matthew Sigman, Berkeley; University of F. Dean Toste, Jeff McKenna Utah

Lewis Base Catalyzed Benzylic Arianna Ayonon*, Christopher T-70 Bromination via Triphenylphosphine San Diego State University Nalbandian, Jeffrey Gustafson Selenide

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Wednesday, June 28, 2017 Poster # Poster Title Authors (*Presenting) Affiliation(s) Universidad de los Andes Study of the Pummerer Reaction as a Yovanny Quevedo-Acosta*, (Colombia), Chemistry W-1 Method for Chiral Thiochromanes Andrés Garzón-Posse, Diego Department, Laboratory of Synthesis Gamba-Sánchez Organic Synthesis, Bio and Organocatalysis

Asymmetric Induction in Hydroacylation Ettore J. Rastelli*, Ngoc T. W-2 by Cooperative Iminium Ion – Transition- University of Houston Truong, Don M. Coltart Metal Catalysis

Manjula Rathnayake *, Jimmie W-3 Merging Photocatalysis and Prenylation Oklahoma State University Weaver

Tetrazolone Based Anion Binders: Proton Hanyang Zhou, Erika Nord, W-4 Ball State University Transfer vs H-Bonding Sundeep Rayat*

Metal-catalyzed Cross-coupling Reactions of Functionalized Organozinc Reagents Heather R. Rensch*, Michael W-5 Bucknell University for the Synthesis of β,β-Disubstituted R. Krout Enones

The Synthesis of Novel Unnatural Amino Barry Rich*, Zain Virk, W-6 Acids in Order to Synthesize Antibiotic Kimberly Brien, Roberto de la Rhodes College Polypeptides Salud Bea

Synthesis of Indene- and Naphthalene- Sibylle Riedel*, Martin E. W-7 Derivatives from Enynols via Furan University of Tübingen Maier Intermediates

Ian J. Rosenstein*, Allison M. Microwave-Mediated Nickel-Catalyzed Eckert, Christopher C. Powell, Department of Chemistry, W-8 Conjugate Addition Reactions of Travis J. Roeder, John R. Hamilton College Arylboronic Acids DeGuardi

Selectively Trapping Residual Vancomycin Brittany Russ*, Ryan Mull, Department of Chemistry, W-9 with Peptide Analogs to Prevent Colonic Yftah Tal-Gan University of Nevada, Reno Bacterial Stress

◊Northern Kentucky University, †Grand Valley KC Russell*◊, Shannon Biros†, State University, A Dispersed REU Program on W-10 Peter Iovine‡, Jeff Katz¶, ‡University of San Diego, Theoretically Interesting Molecules (TIM) ¶ § Kristine Nolan§, Ellen Yezirski∂ Colby College, University of Richmond and ∂Miami University

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Poster # Poster Title Authors (*Presenting) Affiliation(s) Azobenzene Modified Enzyme Inhibitors Karin Rustler*, Matthias University of Regensburg W-11 as Photochromic Modulators for Single- Mickert, Hans-Heiner Gorris, (Germany) molecule Studies Burkhard König

Robert E. Sammelson*, Synthesis of Novel Quinoline-5,8-Dione Department of Chemistry, W-12 Raheleh Ravanfar, Jenny Analogues Related to Lavendamycin Ball State University Nguyen, Justin Giessler

Rishi R. Sapkota*, Jacqueline A Combined Experimental and M. Jarvis, Tanner M. Schaub, New Mexico State W-13 Computational Study of the Cross Marat Talipov, Jeffrey B. University Metathesis of Allylic Sulfones. Arterburn

2-Amidoallyl Cation Intermediacy Mirza A Saputra*, Binod W-14 Towards Enantioselective Beta Nepal, Nitin S. Dange, Rendy Louisiana State University Functionalization of Enamides Kartika

Catalyst Controlled Alkene Stephen R. Sardini*, Professor W-15 Difunctionalization: Regiodivergent Indiana University M. Kevin Brown Arylboration of 1,3-Dienes

Aritra Sarkar*, Bardia Mechanistic Investigation of Soltanzadeh, Roozbeh Yousefi, W-16 (DHQD) PHAL Catalyzed Enantioselective Michigan State University 2 Atefeh Garzan, Dan Chlorination of Olefins Steigerwald, Babak Borhan

Cu-Catalyzed Three-Component Travis L. Buchanan*, Samuel University of Illinois at W-17 Carboamination of Olefins N. Gockel, Kami L. Hull Urbana-Champaign

Diels-Alder/retro-Diels-Alder Sequence Nick Angello*, Ryan Perry, The College of William and W-18 for the Synthesis of 2-Pyridones from Tristan Elmore, Bob Wiley, Mary Diketopiperazines Prof. Jonathan R. Scheerer

Development of Novel Photocatalytic and Sameera M. Senaweera*, Department of Chemistry, W-19 SNAr Reactions for the Facile Access of Jimmie D. Weaver Oklahoma State University Functionalized Multifluorinated Arenes

Department of Chemistry A Nitroso-Mediated Methodology for the Jamie Shaum*, David Fisher, and Biochemistry, W-20 Synthesis of N–O Heterocycles and Amino Miranda Sroda, Luis Limon, University of California, Alcohols Javier Read de Alaniz Santa Barbara

Organic II Course-Based Research W-21 Experience: Isolation of Neurolenin D and Kevin M. Shea* Smith College Synthesis of Analogs

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Poster # Poster Title Authors (*Presenting) Affiliation(s) Yohei Shimizu*, Taiki Fujita, Boron-catalyzed Nucleophilic Activation Yuya Morita, Tomohiro W-22 The University of Tokyo of Carboxylic Acids Yamamoto, Hideoki Nagai, Motomu Kanai

Enantioselective Iridium-Catalyzed Allylic Samantha E. Shockley*, J. California Institute of W-23 Alkylation Reactions of Masked Acyl Caleb Hethcox, Brian M. Stoltz Technology Cyanide Equivalents

Novel Method for the Generation of Munia F. Sowaileh*, Robert A. University of Mississippi W-24 Precursors to Difluoroenolates and Hazlitt, Que-Lynn Tran, David and St. Jude Hospital Exploration of Reactivity A. Colby

The Diverse Reactivity of 1-Aza-2- Ramya Srinivasan*, Matthias W-25 azoniaallene Salts and its Application in University of Vermont Brewer the Total Synthesis of (+)-Ibophyllidine

Regio- and Diastereoselective Trevor Stockdale*, Gregory Western Washington W-26 Samarium(II)-Mediated Allylic Benzoate O'Neil University Reductions

Metal-free Cyclopropanation Of Alkenes Jason Tao*, Carl D. Estrada, W-27 University of Waterloo Using Iodonium Ylides Graham K. Murphy

Selective Perfluoro- and Polyfluoroarylation of Oxazolones; Kip A. Teegardin*, Jimmie D. W-28 Oklahoma State University Synthesis of Unnatural Polyfluorinated α- Weaver Amino Acids

Kristine C. Teppang*, Dillon D. Fluorescence Monitoring of DNA Duplex Burns, Raymond W. Lee, Dr. W-29 Formation by a Chemically Modified San Diego State University Melissa E. Lokensgard, Prof. Cytidine Analogue Byron W. Purse

Sean Toenjes*, Sean Maddox, Structural Optimization of Atropisomeric W-30 Valeria Garcia, Jeffrey San Diego State University Pyrrolopyrimidine RET Kinase Inhibitors Gustafson

Kathryn Trentadue*, Jacob H. Jansen*, Katherine M. Reed, Carbon-Carbon Single Bond Activation Gabriella D. Dyke, Janelle K. W-31 Leading to Oxidative Coupling with Hope College Kirsch, Erik J. T. Phipps, Michael Acceptors Caroline E. Gregerson, Jeffrey B. Johnson

Cysteine Thiyl Radicals as Peptide-Based Jonathan M. Ryss, Amanda K. W-32 Yale University Catalysts for Enantioselective Cyclization Turek*, Scott J. Miller

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Poster # Poster Title Authors (*Presenting) Affiliation(s) Robert Palkovitz, Anthony C. Transfer Hydrogenation by a Hantzsch Franklin and Marshall W-33 O'Donnell, Scott A. Van Amide College Arman*

Palladium Catalyzed Allylation of N- Sandeep R. Vemula*, Dinesh North Dakota State W-34 Heterocyles: An Advancement from Kumar, Gregory R. Cook University Traditional to Allylic C-H Activation!

Design and Synthesis of S-Benzofuran- 3(2H)-ones and their Binding Affinity Nishant Verma*, Dr. Naseem Indian Institute of W-35 Study on Estrogen and Progestron Ahmed, Dr. Sumit Kumar Technology Roorkee Receptors Protein

Modular Synthesis and Reactivity Salim Javed, Dimuthu Profiling of Novel P-Stereogenic Vithanage*, Arghya Ganguly, Department of Chemistry, W-36 Phosphates: One-pot, Sequential Enyne Gihan Dissanayake, Paul R. University of Kansas Ring-Closing Metathesis/Diels-Alder Hanson Reactions

Eun Bin Go, Lee Joon Kim, Toward Biomimetic Syntheses of Shannon P. Wetzler, Kareesa J. W-37 Harvey Mudd College Cryptobeilic and Isocryptobeilic acid D Kron, Geneva E. Miller, David A. Vosburg*

Synthesis of derivatives of the tripodal Brandon G. Wackerle*, Department of Chemistry, W-38 TREN-CMPO ligand to increase Ln and An Michael Hudson*, John E. Grand Valley State extraction efficiency Bender, Shannon M. Biros University, Michigan

†Oakland University and Synthesis of Fluorinated 1,5- Austin Walsh*†, Ariela W. ‡Centre of Molecular and W-39 Benzodiazepines from 2-Fluoro-alk-3-yn- Kaspi-Kaneti†, Roman Macromolecular Studies, 1-ones Dembinski†,‡ Polish Academy of Sciences

Scarlett M. Walton*, Othman Abdulla, Adam D. Clayton, Catalytic sp3-sp3 Coupling of W-40 Duncan M. Gill, Robert A. University of Huddersfield Sulfonamides Faulkner, Craig R. Rice, Joseph B. Sweeney

Photooxidation and Cycloaddition Yuchao Deng, Xiaojing Wei, W-41 Catalyzed by Electron-Rich Aromatic Hui Wang, Yuhan Sun, Harvard Medical School Disulfides Timothy Noel, Xiao Wang*

Fang Wang*, Chanan D. Sessler, Martin Rahm, Sabine Massachusetts Institute of W-42 CF H, a Hydrogen Bond Donor 2 Becker, Jacob M. Goldberg, Technology Stephen J. Lippard

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Poster # Poster Title Authors (*Presenting) Affiliation(s) Alekhya Sama*, Dominique Synthesis of Novel Bioactive W-43 Schols, Kurt Vermeire, Thomas University of Nevada, Reno Triazacyclododecanes W. Bell

Nickel-catalyzed Functionalization of Eric M. Wiensch*, David P. W-44 University of Michigan Silyloxyarenes Todd, John Montgomery

New Perspectives for Lewis Catalyzed Johannes M. Wiest*, M. Kevin W-45 [2+2] Cycloadditions Between Alkenes Indiana University Brown and Allenoates

Alexander Wimmer*, Andreas Visible-Light-Accelerated C-H- W-46 Uwe Meyer, Prof. Dr. University of Regensburg Sulfinylation of Heteroarenes Burkhard König

Department of Chemistry, Iron-Catalyzed Substitution of Paul T. Marcyk*, Latisha R. W-47 Indiana University Unactivated Alcohols by Sulfonamides Jeffries, Silas P. Cook Bloomington

Integrated Process for Biodiesel Michael Wormann*, Martin E. University of Tübingen, W-48 Production Maier Germany

Catalytic Enantioselective Synthesis of Yao Xu*, Michael L. Conner, Indiana University W-49 Cyclobutanes Through [2+2] M. Kevin Brown Bloomington Cycloaddition of Allenes and Alkenes

Feng Xu*, Rich Desmond, Development of Practical Manufacturing Jungchul Kim, Wang Tao, Jake Process Research and Process of Grazoprevir, a Potent NS3/4a W-50 Waldman, Yong-Li Zhong, Development, Merck & Co., Protease Inhibitor for the Treatment of Hongming Li, Jeonghan Park, Inc., Rahway, NJ HCV Paul Devine

Metabolic Profiling of Tea (Camellia Department of Chemistry Jacquelyn Gervay-Hague, W-51 sinensis) Glycolipids using Mass University of California, Crystal S. Ye* Spectrometry Davis

Palladium-catalyzed C–S Couplings of Unprotected Indazoles at Room Charles S. Yeung*, Jacob M. Merck Research W-52 Temperature: Mitigating Ring-opening Ganley Laboratories Isomerization by in situ Deprotonation

Catalytic Enantioselective Yi Yi*, Xingliang Ding, Babak W-53 Desymmetrization of Dienes via Michigan State University Borhan Chlorocyclization

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Poster # Poster Title Authors (*Presenting) Affiliation(s) Emily E. Zerull*, Evan O. 2-Propargyloxypyridines as Precursors to W-54 Romero, Abigail K. Frndak, Calvin College Trisubstituted Indolizines Carolyn E. Anderson

Copper Catalyzed One Pot Indole W-55 Oxidative Dearomatization and Allylic C-H Jun Zhang*, Babak Borhan Michigan State University Oxidation

DBU-catalyzed Regioselective Aldol Okinawa Institute of W-56 Reactions to Synthesize Functionalized Dongxin Zhang*, Fujie Tanaka Science and Technology Molecules Graduate University

Transition Metal Free Dichlorination and Meng Zhao*, Yuanlin Deng, University of Illinois at W-57 Transition Metal Mediated Justin Mohr Chicago Rearrangement

Bin Zheng*, Steven M. Silverman, Sarah E. Steinhardt, Sergei Kolotuchin, Vidya Iyer, Development of a Process for the Friedel- Chemical and Synthetic Junying Fan, Dimitri Skliar, Crafts Acylation, Hydrolysis and Development, Bristol- W-58 Douglas D. McLeod, Michael Amidation of the Azaindole Core in the Myers Squibb Company, Bultman, Jonathan C. Tripp, HIV Attachment Inhibitor BMS-663068 New Brunswick, NJ Saravanababu Murugesan, Jason T. Sweeney, Martin D. Eastgate, David A. Conlon

Iron-Catalyzed Stereoselective Cheng-Liang Zhu*, Deng-Fu W-59 Aminofluorination for Unfunctionalized Georgia State University Lu, Jeffrey D. Sears, Hao Xu Olefins

Visible Light Photocatalysis for the Amandeep Arora*, Jimmie W-60 Generation and Use of Reactive Azolyl Oklahoma State University Weaver Intermediates for Synthesis

Strain Induced Couplings Mediated by Kamaljeet Singh*, Jimmie W-61 Oklahoma State University Visible Light Weaver

Borane-promoted Catalytic Asymmetric Veronika M. Shoba*, James M. University of Nebraska- W-62 Hydrogenation of Tri- and Takacs Lincoln Tetrasubstituted Alkenes

X-Ray Spectroscopic Characterization of J. David Ricker*, Yousoon Lee, W-63 Organocobalt Intermediates Active in the University of Nevada, Reno Laina M. Geary, Jason Shearer Pauson-Khand Reaction

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Poster # Poster Title Authors (*Presenting) Affiliation(s) Enantioselective Gamma- and Delta- Gia L. Hoang*, Shao-Di Yang, borylation of Carbonyl Derivatives: University of Nebraska- W-64 Sean M. Smith, James M. Synthesis, Mechanistic Insights, and Lincoln Takacs Applications

Investigations of Organometallic, Organocatalytic, and Base Mediated Austin T. Kelly*, Annaliese K. University of California, W-65 Methods for the Hydrolysis of 1,3- Franz Davis Dihydro-disiloxanes

Regio- and Diastereoselective Trevor Stockdale*, Gregory Western Washington W-66 Samarium(II)-Mediated Allylic Benzoate O’Neil University Reductions

Tyler Davis*, John Limanto, Artis Klapars, Daniel DiRocco, John Chung, Byron Simmons, Alan Hyde, Susan Zultanski, Development of the 2nd Generation Peter Maligres, Feng Peng, Process Research and W-67 Commercial Route to an HCV NS5b Wenyong Chen, Jamie Development, Inhibitor MK-3682 Dropinski, Yi Ning, Ji Chen, Merck and Co. Jacob Waldman, Jake Song, Ed Sherer, Mikhail Reibarkh, Frank Bernadoni, Mona Larsen, Aaron Moment

Chandrima Majumdar*, Nucleobase Analogs as Probes for Amelia Manlove, Paige University of California, W-68 Substrate Recognition and Repair by DNA McKibbin, Michelle Hamm, Davis Glycosylase MutY Sheila S. David

Fragment Coupling and Constructing Peng Zhao*, Yuriy Sluskyy, University of California, W-69 Quaternary Carbon Stereocenters Using Christopher Jamison, Larry Irvine Carbon Radicals Overman

Photocatalytic Prenylation of W-70 Sonal Priya*, Jimmie Weaver Oklahoma State University Perfluoroarenes

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