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ORGANIC CHEMISTRY Alkynes

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ORGANIC CHEMISTRY Alkynes University of Michigan new functional groups. (3) Developing novel routes for functionalizing readily available organic building blocks DEPARTMENT OF CHEMISTRY such as alkenes and alkynes. (4) Exploring the reduc- tive coupling of aldehydes and alkynes or enones and ORGANIC CHEMISTRY alkynes. Recent studies have demonstrated strategies involving redox isomerization to avoid the use of reduc- Graduate Program ing agents in processes of this type. (5) The discovery of new glycosylation methods and their application in collaborative projects involving enzymatic C-H oxida- tion reactions. Traditional Synthetic Novel C–H Bond Approach Functionalization Approach Fluorinated amino acids can be used to make super-stable “Tef- O O N O NH N lon” proteins; here the interior of a small protein is packed with the Michigan offers a diverse selection of research oppor- 2 Br 1. Br cat. PdII fluorous amino acid hexafluoroleucine (Marsh). O N tunities in Organic Chemistry with particular strengths Y Y Y N 2. NH3/MeOH Oxidant–X in Organometallic Chemistry, Organic Synthesis, Bioor- X X H 3. CH3I ganic Chemistry, and Organic Materials. Our innovative treatment of autoimmune diseases and cancer. (3) Anti-anxiety research rotation program allows students to explore Anti-convulsant Developing and applying chemical tools to study a range of exciting possibilities before choosing an Palladium-catalyzed C-H functionalization of an arene (Sanford). the role of oxidants as signaling molecules and the advisor. Specific research projects in each area are biological basis of aging. (4) Elucidating catalytic highlighted below. mechanisms and essential active site features of me- talloenzymes and ribozymes, including protein farnes- Organic Synthesis yltransferase, UDP-3-O-acyl-GlcNAC deacetylase, his- R3 H tone deacetylase and ribonuclease P. These studies O Ni(0) O R2 Designing efficient synthetic routes to complex organic + should enhance our ability to design potent inhibitors + O R2 R3 molecules remains a challenge. At Michigan, several H R4 R of these enzymes useful for the treatment of cancer 1 R1 O R4 research groups are working on total syntheses using or bacterial infections. (5) Exploring the interface methods developed in their labs. Recent synthetic Nickel-catalyzed coupling of an aldehyde, alkyne and enone via redox between biological macromolecules and materials isomerization (Montgomery). targets include aigialomycin D, cephalotaxine, and chemistry through the de-novo design of extensively aphanorphine. fluorinated “Teflon” proteins. Such proteins exhibit useful new properties such as increased thermal sta- Organometallic Chemistry OH O CH 3 bility, resistance to unfolding in organic solvents, and Transition-metal mediated bond formation can be a O O resistance to degradation by proteases. versatile and efficient transformation in any organic N H HO O synthesis. At Michigan, several research groups are fo- N Me OH HO cused on the use of transition metals in reaction discov- HO OH Me ery, synthetic methodology development, mechanistic OMe aigialomycin D Cephalotaxine Aphanorphine chemistry, and complex molecule synthesis. Highlights of ongoing research projects include: (1) Developing new transition-metal catalyzed reactions for the ste- Bioorganic Chemistry reoselective synthesis of saturated heterocycles such as tetrahydrofurans and pyrrolidines. (2) Discovering Research efforts in Bioorganic Chemistry at Michigan methods to transform inert carbon-hydrogen bonds into focuses on applying chemical principles, particularly those of organic chemistry, to solve problems in human health. Highlights of ongoing research projects include: (1) Developing strategies for reprogramming gene ex- O O Br cat. Pd2(dba)3 pression using small molecules, both natural products and cat. dppb N NH Ph ‘designer’ molecules. These molecules are being used Ph + NaOtBu, Toluene N 105 °C as mechanistic probes of eukaryotic transcription as well 82% yield N as prototypes for transcription-targeted therapeutics for Detecting redox-regulated proteins in living cells. (A) Sulfenic acid >20:1 dr post-translational modifications are selectively detected via the diseases ranging from diabetes to cancer. (2) Identify- cell-permeable probe DAz-1. (B) Visualization of protein sulfenic Palladium-catalyzed reaction of an γg-amino olefin and an aryl ing novel molecular targets and small molecules for the acids in MEF cells treated with DAz-1 (right) or untreated (left) bromide (Wolfe). (Carroll). O Organic Materials Life in Ann Arbor Organic Materials research at Michigan is focused The University of Michigan offers a rich intellectual envi- Chemistry on creating functional properties through synthetic ronment. Opportunities for research and collaboration modifications to polymers and small-molecules. in Organic Chemistry are enhanced by top-ranked pro- Highlights of ongoing research projects include: at the grams in Medicinal Chemistry, Biochemistry, and the Life rganic (1) Developing techniques to control the process Sciences Institute. of crystallization using organic polymers as phase directors with the goal of making materials with im- The University is located in Ann Arbor, a small city of 110,000, University of proved function. Combinatorial materials chemistry combining the comfort and charm of a college town with plays a vital role in these efforts. (2) Developing nov- the vivid cultural life of a large city. el routes for the efficient production of new mem- Michigan bers of conjugated oligomers and polymers with planar structural constraints, such as fused oligothio- Further Information phenes, and For more information about specific research interests, studying their go to: www.umich.edu/~michchem. Please feel free to behavior in contact faculty directly: the solid state as it relates Kate S. Carroll [email protected] to important Brian Coppola [email protected] device appli- Carol Fierke [email protected] C cations such Gary Glick [email protected] as organic Masato Koreeda [email protected] thin film tran- Anna Mapp [email protected] sistors (OTFTs). Neil Marsh [email protected] These struc- Adam J. Matzger [email protected] ture types Optical microscope image of a novel small- Anne McNeil [email protected] also find ap- molecule based hydrogel (McNeil). John Montgomery [email protected] hemistry plication in Melanie Sanford [email protected] the construction of porous solids for applications David Sherman [email protected] ranging from gas storage to catalysis. (3) Design- Edwin Vedejs [email protected] ing new molecules that induce hydrogelation in John P. Wolfe [email protected] the presence of an analyte for use in chemical Ronald Woodard [email protected] and biological sensing. (4) Developing living po- lymerization methods for the synthesis of new con- jugated polymer architectures for optoelectronic How to Apply applications. Application to the Chemistry Graduate Program at the University of Michigan is online at www.umich.edu/ ~michchem/graduate/ S S S S S S S For questions regarding admission, see www.umich. edu/~michchem or contact the department by S S S S S S Website: www.umich.edu/~michchem S S C9H19 Email: [email protected] S S Phone: toll free 888-999-2436 or 734-764-7278 C9H19 C H S Fax: 734-647-4865 S 9 19 C9H19 n n Methodology development for the synthesis of conjugated polymers and oligomers of fused-ring thiophene compounds (Matzger). cover: Highlights of research in Organic Chemistry at Michigan. 2008 www.umich.edu/~michchem/.
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