The Way of Synthesis: Evolution of Design and Methods for Natural Products

"I think, as will many organic chemists, that the Hudlicky book will be the Bible of synthetic organic chemistry, the past, the present and the future. A hallmark publication." —Victor Snieckus This two-colored textbook presents not only synthetic ways to design organic compounds, it also contains a compilation of the most important total synthesis of the last 50 years with a comparative view of multiple designs for the same targets. It explains different tactics and strategies, making it easy to apply to many problems, regardless of the synthetic question in hand. Following a historical view of the evolution of synthesis, the book goes on to look at principles and issues impacting synthesis and design as well as principles and issues of methods. The sections on comparative design cover classics in terpenes and alkaloid synthesis, while a further section covers such miscellaneous syntheses as Maytansine, Palytoxin, Brevetoxin B and Indinavir. The whole is rounded off with a look at future perspectives and, what makes this textbook extraordinairy, with personal recollections of the chemists, who synthesized these fascinating compounds. With its attractive layout highlighting key parts and tactics using a second color, this is a useful tool for organic chemists, lecturers and students in chemistry, as well as those working in the chemical industry.

Table of Contents:
Foreword VII Preface XIII Part 1 Introduction 1 1.1 History of Synthesis 3 1.2 Milestones in Structure Elucidation 23 1.3 Milestones in Organic Synthesis 41 Part 2 Strategy and Tactics 79 2.1 Introduction 81 2.2 Principles and Issues Impacting Synthesis (Strategy) 87 2.3 Principles and Issues Impacting Design – Dimensional Analysis (Strategy) 129 2.4 Principles and Issues of Methods (Tactics) 165 Part 3 Comparative Design: Classics in Terpene Synthesis 205 3.1 Introduction 207 3.2 Juvenile Hormones 217 3.3 Cedrenes 229 3.4 Zizaanes 255 3.5 Hydroazulenes 277 3.6 Vernolepin 341 3.7 Triquinanes 361 3.8 Compactin 431 3.9 Aphidicolin 449 3.10 Miscellaneous Terpenes 469 3.11 Taxol 499 Part 4 Comparative Design: Classics in Alkaloid Synthesis 525 4.1 Introduction 527 4.2 Lycopodium Alkaloids 573 4.3 Daphniphyllum Alkaloids 603 4.4 Pyrrolizidine Alkaloids 617 4.5 Cephalotaxus Alkaloids 655 4.6 Amaryllidaceae Constituents 689 4.7 Morphine 727 4.8 Indole Alkaloids 759 Part 5 Miscellaneous Compounds 843 5.1 Introduction 845 5.2 Palytoxin 891 5.3 Indinavir 909 Part 6 Outlook 917 6.1 Introduction 919 6.2 A Short History of Accomplishments in Synthesis 921 6.3 Factors Influencing the Practice of Organic Synthesis 923 Part 7 Acknowledgments 945 Part 8 Appendix 947 8.1 Abbreviations, Acronyms, and Symbols 949 8.2 Guide to the Literature 953 Subject index 957 Author index 995 Index of personal recollection 1003

About the Author :
Tomas Hudlicky was born in Prague, Czechoslovakia, and emigrated to the US in 1968. He received his PhD in 1977 under Professor Ernest Wenkert, and subsequently spent a year at the University of Geneva working under Professor Wolfgang Oppolzer on the synthesis of isocomene. He began his academic career in 1978 at the Illinois Institute of Technology, before moving to Virginia tech in 1982 and then the University of Florida in 1995. In 2003, he accepted a chair at Brock University where he is currently professor of organic synthesis and biocatalysis. Professor Hudlicky's research interests include the development of enantioselective synthetic methods, bacterial dioxygenase-mediated degradation of aromatics and the isolation of chiral metabolites for use in asymmetric synthesis. Josephine Wiley Reed was born and raised in North Carolina, receiving her PhD under Professor David Kingston at Virginia Tech in 1988. She holds a BA in biology with chemistry minor from the Appalachian State University and a BA in English from the University of North Carolina in Greensboro. She has taught organic chemistry courses at Virginia Tech and has held the position of Senior Research Associate at Virginia Tech, University of Florida and Brock University since 1989. She has also served as the editorial assistant for the North American Editorial Office of J. Chem. Soc. Perkin Trans 1 and 2, as a member of the organizing committee for the Symposium on the Latest Trends in Organic Synthesis, and as a consultant to TDC Research, Inc, a custom synthesis company.

Review :
"Hudlick and Reed produced a fascinating read featuring numerous epigraphs, quotations, and personal remarks for synthetic chemists at all levels." (CHOICE, February 2008) "...The Way of Synthesis provides much information for its price."  (Angewandte International Edition, December 2007) "Hudlicky hat ein sehr persönliches Buch geschaffen, das sich an einigen Stellen spannend liest. Im Gegenzug zu Nicolaous "Classics in Total Synthesis" mit detaillierten Abhandlungen einiger Zwischenschritte wird in "The Way of Synthesis: Evolution of Design and Methods for Natural Products" eine eher gesamtheitliche Betrachtung gegeben, die auch vor philosophischen Fragestellungen nicht halt macht. Fortgeschrittene Studenten, die sich fragen, auf welchem Arbeitsgebiet sie promovieren wollen, werden genauso eine Antwort finden, wie Personen, welche sich für Taktiken und Strategien in der Totalsynthese interessieren." http://www.organische-chemie.ch/Buch/352731444X.htm Nov. 07 "Das Buch kann allen akademischen Wissenschaftlern im Bereich der organischen Chemie empfohlen werden, die Interesse an historischen Aspekten der Totalsynthese haben," Angewandte Chemie 2008/120/1