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Studies in Meroterpenoid Synthesis

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Studies in Meroterpenoid Synthesis Studies in Meroterpenoid Synthesis A thesis presented by Jonathan W. Lockner to The Scripps Research Institute Graduate Program in partial fulfillment of the requirements for the degree of Doctor of Philosophy in the subject of Chemistry for The Scripps Research Institute La Jolla, California November 2011 1 UMI Number: 3507067 All rights reserved INFORMATION TO ALL USERS The quality of this reproduction is dependent on the quality of the copy submitted. In the unlikely event that the author did not send a complete manuscript and there are missing pages, these will be noted. Also, if material had to be removed, a note will indicate the deletion. UMI 3507067 Copyright 2012 by ProQuest LLC. All rights reserved. This edition of the work is protected against unauthorized copying under Title 17, United States Code. ProQuest LLC. 789 East Eisenhower Parkway P.O. Box 1346 Ann Arbor, MI 48106 - 1346 © 2011 by Jonathan W. Lockner All rights reserved. 2 Thesis Acceptance Form 3 Acknowledgements As a high school student in Plainfield, Illinois, I had the benefit of learning chemistry from Mr. Hill. He supplemented my experience with “Semi-Micro Qualitative Analysis” – allowing me to perform simple chemistry experiments after school. As an undergraduate at the University of Illinois at Urbana-Champaign, I had the opportunity to carry out synthetic organic chemistry research in the laboratory of Professor Robert M. Coates. I am indebted to him, as well as Dr. Chad Davis (then a graduate student and my mentor), for their influence in setting me on the path of scientific research. My first employment was at Pharmacia in Kalamazoo, Michigan. I benefited from the attention afforded me by Dr. Christina Harris, my supervisor during the short time we all enjoyed there prior to the “diaspora” that came with the Pfizer acquisition. I still have fond memories of discussing selected chapters of “Classics in Total Synthesis.” I will never forget the morning we were working in the lab and learned (via internet) that a plane had crashed into the World Trade Center. Despite the negative connotation that comes with Pfizer for its ruthless decade of acquisitions, I am supremely grateful for its bearing on my life. This boy from the Midwest might never have ventured out to California, were it not for the invitation to transfer to the Pfizer site in La Jolla. I am indebted to Dr. Rob Kania and Bob Hoffman, who were my supervisors, and to Simon Planken, from whom I learned much while sharing a lab bay with him. A special thanks also goes to Dr. Steve Tanis, who was always willing to “shoot the s#$t” with me. It is rare to find an individual with both a towering intellect and yet a down-to-earth, approachable personality. 4 Given their co-location on adjacent mesas, I pressed the powers-that-be at Pfizer to participate in courses at The Scripps Research Institute. At one point, I visited Professor Phil Baran in his office, and, for better or for worse, he asked me “So when are we going to see you in this lab?” I took him up on the veiled invitation, and took a huge pay cut, to become “a monk” (one of the many metaphors I would hear uttered by Phil in the years that ensued). Of the many valuable lessons I have learned from Phil over the past five years, certainly this list includes: Be willing to work really, really hard; Develop and maintain a “killer instinct”; Strive to be innovative and opportunistic; Expect dedication and quality from yourself and others, and good things will happen. For everyone in the Baran Lab that had to put up with my moodiness, and my obsessive-compulsive nature – thank you for your patience. I think that graduate school, in its most stressful seasons, brought out the worst in me. Thanks for putting up with me. A special thanks goes to Dr. Mike DeMartino, with whom I shared a hood during my first two years in the Baran Lab. Dr. Jeremy Richter was an indispensable source of reassurance in my most trying times. Dr. Kyle Eastman always provided an injection of energy and enthusiasm that I only wish could come naturally in me. Dr. Ke Chen was an incredible example of a hard worker, a generous lab mate, and fun office neighbor. Thank you to the members of my thesis committee: Professor Jin-Quan Yu, Professor Kim Janda, Professor Floyd Romesberg, and Professor Carlos Guerrero. All of you are tremendous examples of top-flight scientists, and it has been a privilege to be shepherded by you over the years. 5 During the summer of 2009, I served as a mentor for Marcus Bray, a student at Torrey Pines High. During the summer of 2011, I served as a mentor for Sylvia Chen, an undergraduate research fellow from University of Wisconsin, Madison. What great perspective I gained from those experiences. I also thank those with whom I worked in a direct manner: Dr. Elena Petricci, Paul Hernandez, Rune Risgaard, and Dr. Darryl Dixon. Without the various support facilities such as the NMR lab (Dee-Hua Huang, Laura Pasternak) and the HRMS lab (Bill Webb and colleagues), research progress would be markedly slower. The Scripps Research Institute benefits immensely from these expertly run labs that allow the chemist to elucidate the constitution of molecules he prepares. Additionally, I am indebted to the skilled colleagues at UCSD’s X-ray lab, led by Professor Arnie Rheingold, who solved numerous crystal structures, thereby obviating the need for time-consuming multidimensional NMR experiments and data analysis. Scientific research, and training of young scientists, would simply not be possible without the generous financial support of government and private agencies. I personally thank Amgen, Bristol-Myers Squibb, and Leo Pharma for their funding which enabled me to carry out my research in the Baran Lab. To those friends outside the lab, whom I rarely saw while a graduate student working long hours: thank you for your patience and understanding. I thank the entire Koinonia family, especially Jen Ernest, Sarah Kim, Theresa Abueg, Marieke Jones, Nathan and Sarah Venzara, Nick Taylor, Kayla Weisman, Michele Fujioka, Paul Carter, Derek and Lacey Joseph, Brandon and Ariane Fries, David and Gracie Rhoads. Mom (Phyllis Vancas) – so much of who I am is because of you. Thank you for working three jobs while a single mother raising two sons. My older brother, Randy, and 6 sister-in-law Kelly, and nephews (Justin, Nathan, Logan) – you are all very precious to me! My step-mom, Mary – thank you for the Omaha Steaks care package every Christmas! My younger brother, Aaron – be kind to your mother! Thank you to my father-in-law and mother-in-law (Danny and Julie Cruz) for making me truly feel like a son. Birthday privilege is a wonderful tradition! I am honored to be a part of your family. Jonathan Cruz, Jennie, Gabby, and Zoe – I love you all very much! Ernie and Patti Orderica, and the rest of my extended family here in San Diego – I look forward to more Friday Clubs, Easter Bonnets, Turkey Bowls! Don and Kathy Knox – thank you for your support! Alyssa Janine – amazing, beautiful, charismatic, delightful, expressive, fun, gregarious, hilarious, intelligent, joyful, kind, lovely, marvelous, naturally beautiful, optimistic, patient, quotable, resourceful, sweet, tender, unconditional, vivacious, witty, xenophilic, youthful, zany – you are all of these, and so much more. Thank you for saying “I do.” We made it. Your enduring and constant love and support is the reason I made it through with my wrists intact. 7 Table of Contents Acknowledgements ............................................................................................................. 4 Table of Contents ................................................................................................................ 8 List of Figures ..................................................................................................................... 9 Abbreviations .................................................................................................................... 12 Abstract ............................................................................................................................. 16 Chapter 1. Review of Meroterpenoids .............................................................................. 17 Chapter 2. Studies in Meroterpenoid Synthesis ................................................................ 31 Chapter 3. Radical Chemistry Applied to Meroterpenoid Synthesis ................................ 65 Experimental ..................................................................................................................... 82 References ....................................................................................................................... 198 Appendix A. Spectra ....................................................................................................... 207 Appendix B. X-ray Crystallographic Data ...................................................................... 305 Curriculum Vitae ............................................................................................................ 336 Table of Contents 8 List of Figures Figure 1-1. Mori’s synthesis of hongoquercin B .............................................................. 17 Figure 1-2. Kende’s synthesis of stachybotrylactam ........................................................ 18 Figure 1-3. Katoh’s synthesis of kampanol ABCD ring system ....................................... 18 Figure 1-4. Mori’s synthesis of stypoldione ....................................................................
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