Strategies and Tactics in Organic Synthesis, Vol. 4

Michael Harmata (Ed.)9780124502833, 0-12-450283-0, 0-12-450287-3

A classic in the area of organic synthesis, Strategies and Tactics in Organic Synthesis provides a forum for investigators to discuss their approach to the science and art of organic synthesis. Rather than a simple presentation of data or a second-hand analysis, we are given stories that vividly demonstrate the power of the human endeavour known as organic synthesis and the creativity and tenacity of its practitioners. First hand accounts of each project tell of the excitement of conception, the frustration of failure and the joy experienced when either rational thought and/or good fortune give rise to successful completion of a project. In this book we learn how synthesis is really done and are educated, challenged and inspired by these stories, which portray the idea that triumphs do not come without challenges. We also learn that we can meet challenges to further advance the science and art of organic synthesis, driving it forward to meet the demands of society, in discovering new reactions, creating new designs and building molecules with atom and step economies that provide solutions through function to create a better world. – Personal accounts of research in organic chemistry. – Written by internationally renowned scientists. – Details state of the art organic synthesis.

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Table of contents :
Content:
Contributors
Pages xiii-xiv

Foreword
Pages xv-xvi
Paul A. Wender

Preface
Pages xvii-xviii
Michael Harmata

Dedication
Page xix

Chapter 1 Methodology validation and structure correction by total synthesis: The case of the clerodane diterpenoid, sacacarin Original Research Article
Pages 1-18
Robert B. Grossman, Ravindra M. Rasne

Chapter 2 Total synthesis of (±)-cylindrospermopsin Original Research Article
Pages 19-39
Barry B. Snider, Chaoyu Xie

Chapter 3 The total synthesis of (-)-Arisugacina A Original Research Article
Pages 41-70
Richard P. Hsung, Kevin P. Cole

Chapter 4 Total synthesis of kainoids by dearomatizing anionic cyclization Original Research Article
Pages 71-96
Jonathan Clayden

Chapter 5 Total synthesis of jatrophatrione, an unprecedented [5.9.5] tricyclic antileukemic diterpene Original Research Article
Pages 97-131
Leo A. Paquette

Chapter 6 Alkynyliodonium salts in organic synthesis Original Research Article
Pages 133-170
Ken S. Feldman

Chapter 7 How to thread a string through the eye of a molecular needle: Template synthesis of interlocked molecules Original Research Article
Pages 171-210
Michael Kogej, Pradyut Ghosh, Christoph A. Schalley

Chapter 8 Total synthesis of spongistatin 1 (altohyrtin a): A tale of ten aldols Original Research Article
Pages 211-245
Ian Paterson, Mark J. Coster

Chapter 9 The ring-closing metathesis approach to fumagillol Original Research Article
Pages 247-267
Jacques Eustache, Pierre Van de Weghe

Chapter 10 Devising an especially efficient route to the ‘Miracle’ 1 nutrient coenzyme Q10 Original Research Article
Pages 269-292
Bruce H. Lipshutz

Chapter 11 Total synthesis of lipid I and lipid II: Late-stage intermediates utilized in bacterial cell wall biosynthesis Original Research Article
Pages 293-313
Michael S. VanNieuwenhze

Chapter 12 Ring rearrangement metathesis (RRM) — A new concept in piperidine and pyrrolidine synthesis Original Research Article
Pages 315-346
Sandeep Basra, Siegfried Blechert

Chapter 13 Catalytic asymmetric total synthesis of (-)-strychnine and fostriecin Original Research Article
Pages 347-363
Masakatsu Shibasaki, Motomu Kanai, Takashi Ohshima

Chapter 14 The synthesis of (⇠)-strychnine via a cobalt-mediated [2 + 2 + 2]cycloaddition Original Research Article
Pages 365-405
K. Peter C. Vollhardt, Michael J. Eichberg

Index
Pages 407-415