Designing Synthetic Methods and Natural Products Synthesis
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Designing Synthetic Methods and Natural Products Synthesis
Lives in Chemistry – Lebenswerke in der Chemie, Vol. 9
(2024)
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About The Author
Larry E. Overman, born in Chicago in 1943, is Distinguished Professor of Chemistry at the University of California, Irvine. He was the recipient of the Arthur C. Cope Award in 2003, and he was awarded the Tetrahedron Prize for Creativity in Organic Chemistry for 2008. Overman's research is focused on the development of new chemical reactions, particularly transition metal catalyzed reactions, and the application of those reactions toward the synthesis of natural products. He is most known for the Overman rearrangement, a Claisen rearrangement of allylic alcohols to give allylic trichloroacetamides.Abstract
LARRY E. OVERMAN, born in 1943 in Chicago, had joined the newly founded Faculty of Chemistry, University of California, Irvine in 1971. It became his homebase for more than 50 years until his retirement as Distinguished Professor of Chemistry, Emeritus.How come that he and his wife had chosen Irvine? That over 300 graduate students and postdocs have chosen his lab? That he served also as Chair of the Chemistry Section of the US National Academy of Science, as a founder and consultant in the pharmaceutical industry? Who were his mentors, his professional friends? Why did he early on chase »new chemical reactivity« after his first unexpected discovery? Which of his natural product total syntheses are textbook knowledge today? Who of his students became leaders, even a Nobel Laureate? Larry provides answers.He managed challenges with impressive rigor and elegance. His students praise him and his unique »Let’s see what happens« and »research is a group endeavor« approach!l-i-c.org
Table of Contents
| Section Title | Page | Action | Price |
|---|---|---|---|
| Lives in Chemistry | 3 | ||
| Published titles in this series | 4 | ||
| Imprint | 6 | ||
| Table of Contents | 8 | ||
| Preface | 11 | ||
| 1 Childhood and Education | 15 | ||
| 1.1 Family and schooling | 17 | ||
| 1.2 Undergraduate studies | 24 | ||
| 1.3 Graduate studies | 27 | ||
| 1.4 Postdoctoral studies | 33 | ||
| Further Reading | 38 | ||
| 2 The 1970s: Early Discoveries | 39 | ||
| 2.1 Initiating my research career and the discovery of the Overman rearrangement | 41 | ||
| 2.2 Thermal rearrangements | 48 | ||
| 2.3 Diels-Alder reactions and the total synthesis of pumiliotoxin C | 50 | ||
| Fashions in Research | 52 | ||
| 2.4 Total synthesis of gephyrotoxin and the invention of the aza-Cope Mannich reaction | 54 | ||
| 2.5 Catalytic allylic rearrangements | 57 | ||
| 2.6 Teaching, mentoring, and life at UC Irvine in the 1970s | 58 | ||
| 2.7 Early Participation in Scientific Conferences | 62 | ||
| Further Reading | 64 | ||
| 3 The 1980s and 90s: Heterocyclization Reactions | 65 | ||
| 3.1 My growing involvement in natural products total synthesis | 67 | ||
| 3.2 Iminium ion cyclizations of vinylsilanes and alkynes: synthesis of poison-frog alkaloids | 75 | ||
| 3.3 Pinacol-terminated cationic cyclization reactions | 80 | ||
| 3.4 Sabbatical in Hannover, Germany, 1985 | 89 | ||
| Further Reading | 94 | ||
| 4 The 1980s, 90s and 2000s: Pd-Catalyzed Reactions | 95 | ||
| 4.1 Intramolecular Heck reactions | 97 | ||
| 4.2 Catalytic enantioselective intramolecular Heck reactions | 109 | ||
| Choosing Natural Product Total Synthesis Targets | 118 | ||
| Speculative total synthesis projects | 121 | ||
| 4.3 Catalytic enantioselective reactions of alkenes | 121 | ||
| 4.4 1993 Was a Special Year | 127 | ||
| Adjusting How to Manage My Research Group | 127 | ||
| Further Reading | 129 | ||
| 5 The 1990s and 2000s: Alkaloid Total Synthesis | 131 | ||
| 5.1 Tethered Biginelli reactions and guanidinium alkaloids | 133 | ||
| 5.2 Sarain A | 143 | ||
| 5.3 Epidithiodioxopiperazine (ETP) natural products and tricyclic analogs | 150 | ||
| 5.4 Solvent Purification Systems | 156 | ||
| Further Reading | 158 | ||
| 6 Fragment Coupling with Tertiary-Carbon Radicals | 159 | ||
| 6.1 Investigations of tert-butyl analogs of macfarlandin E | 161 | ||
| 6.2 Total synthesis of (-)-aplyviolene: fragment-coupling reactions of tertiary-carbon radicals | 165 | ||
| Further Reading | 174 | ||
| 7 Professional Activities | 175 | ||
| 7.1 Organic Reactions and Organic Syntheses | 177 | ||
| 7.2 U. S. National Academy of Sciences | 182 | ||
| 7.3 Industrial associations | 184 | ||
| 7.4 Sabbaticals and visiting professorships | 187 | ||
| Further Reading | 188 | ||
| 8 Coworkers, Friends, Hobbies, and My Family | 189 | ||
| 8.1 Coworkers made it possible and enjoyable | 191 | ||
| 8.2 Thoughts on building a research group and mentoring | 194 | ||
| 8.3 David MacMillan, 2021 Chemistry Nobel Prize | 196 | ||
| 8.4 My choice to remain at UC Irvine for my academic career | 198 | ||
| 8.5 Family, friends, recreation and hobbies | 201 | ||
| 8.6 Joanne and our family | 203 | ||
| Appendix | 207 | ||
| Afterword | 209 | ||
| Acknowledgement | 210 | ||
| Vita | 211 | ||
| Chemistree | 212 | ||
| Holographs | 215 | ||
| Publications | 226 | ||
| U. S. Patents | 244 | ||
| Links and literature | 247 | ||
| Image sources | 249 | ||
| Index | 250 | ||
| Reactions from our readers | 254 | ||
| Titles in this series | 255 |