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Adopting his didactically skillful approach, K.C. Nicolaou compiles in this textbook the important synthetic methods that lead to a complex molecule with valuable properties. He explains all the key steps of the synthetic pathway, highlighting the major developments in blue-boxed sections and contrasting these to other synthetic methods. A wonderful tool for learning and teaching and a must-have for all future and present organic and biochemists.…mehr

Produktbeschreibung
Adopting his didactically skillful approach, K.C. Nicolaou compiles in this textbook the important synthetic methods that lead to a complex molecule with valuable properties. He explains all the key steps of the synthetic pathway, highlighting the major developments in blue-boxed sections and contrasting these to other synthetic methods. A wonderful tool for learning and teaching and a must-have for all future and present organic and biochemists.
  • Produktdetails
  • Verlag: Wiley-VCH / Wiley-VCH GmbH
  • Artikelnr. des Verlages: 1132957 000
  • Erscheinungstermin: 9. Februar 2011
  • Englisch
  • Abmessung: 256mm x 194mm x 33mm
  • Gewicht: 1667g
  • ISBN-13: 9783527329571
  • ISBN-10: 3527329579
  • Artikelnr.: 30685972
Autorenporträt
K.C. Nicolaou holds joint appointments at The Scripps Research Institute, where he is the Chairman of the Department of Chemistry and holds the Darlene Shiley Chair in Chemistry and the Aline W. and L.S. Skaggs Professorship of Chemical Biology, and the University of California, San Diego, where he is Distinguished Professor of Chemistry. His impact on chemistry, biology and medicine flows from his research works in chemical synthesis and chemical biology described in numerous publications and patens. For his contributions to science and education, he was elected Fellow of the New York Academy of Sciences, Fellow of the American Academy of Arts and Sciences, Member of the National Academy of Sciences, USA, Member of the German Academy of Sciences Leopoldina, and Corresponding Member of the Academy of Athens, Greece. He is the recipient of many prizes, awards and honors. Jason S. Chen received his A.B. and A.M. degrees in Chemistry from Harvard University in 2001. After two years as a medicinal chemist at Enanta Pharmaceuticals, he began graduate studies at The Scripps Research Institute under the guidance of Professor K.C. Nicolaou. He received a National Defense Science and Engineering Graduate fellowship, and completed his Ph.D. studies in 2008. He currently is a post-doctoral fellow in Professor Nicolaou's laboratory.
Inhaltsangabe
INTRODUCTION: THE ADVANCING FIELD OF TOTAL SYNTHESIS Targets Strategies and Methods Classics in Total Synthesis III TETRODOTOXIN Introduction Kishi's Retrosynthetic Analysis and Strategy Kishi's Total Synthesis Du Bois' Retrosynthetic Analysis and Strategy Du Bois' Total Synthesis Conclusion DISCODERMOLIDE Introduction Retrosynthetic Analysis and Strategy Total Synthesis Conclusion AZASPIRACID
1 Introduction Nicolaou's Retrosynthetic Analysis and Strategy Nicolaou's Total Synthesis Evans' Retrosynthetic Analysis and Strategy Evans' Total Synthesis Conclusion THIOSTREPTON Introduction Retrosynthetic Analysis and Strategy Total Synthesis Conclusion PENTACYCLOANAMMOXIC ACID METHYL ESTER Introduction First
Generation Retrosynthetic Analysis and Strategy First
Generation Total Synthesis Second
Generation Retrosynthetic Analysis and Strategy Second
Generation Total Synthesis Conclusion LITTORALISONE, OSELTAMIVIR (TAMIFLU®), AND HIRSUTELLONE B Introduction Introduction to Littoralisone Total Synthesis of Littoralisone Introduction to Oseltamivir (Tamiflu®) Total Synthesis of Oseltamivir (Tamiflu®) Introduction to Hirsutellone B Total Synthesis of Hirsutellone B Conclusion RUBICORDIFOLIN AND RUBIONCOLIN B Introduction Retrosynthetic Analysis of Rubicordifolin Total Synthesis of Rubicordifolin Retrosyntheticd Analysis of Rubioncolin B Total Synthesis of Rubioncolin B Conclusion CYANTHIWIGINS U AND F Introduction Phillips' Retrosynthetic Analysis and Strategy Phillips' Total Synthesis Stolz' Retrosynthetic Analysis and Strategy Stoltz' Total Synthesis Conclusion STEPHACIDIN B Introduction Myers' Retrosynthetic Analysis and Strategy Meyers' Total Synthesis Baran's Retrosynthetic Analysis and Strategy Baran's Total Synthesis Williams' Retrosynthetic Analysis and Strategy Williams' Total Synthesis Conclusion ABYSSOMICIN C AND ATROP
ABYSSOMICIN C Introduction Sorensen's Retrosynthetic Analysis and Strategy Sorensen's Total Synthesis of Abyssomicin C Nicolaou's Retrosynthetic Analysis and Strategy Nicolaou's Total Synthesis of Abyssomicin C and atrop
Abyssomicin C Conclusion TETRACYCLINE Introduction Retrosynthetic Analysis and Strategy Total Synthesis Conclusion BISANTHRAQUINONE NATURAL PRODUCTS Introduction Retrosynthetic Analysis and Strategy Toward 2,2'
epi
Cytoskyrin A, Rugulosin, and Rugulin Total Synthesis of 2,2'
epi
Cytoskyrin A, Rugulosin, and Rugulin Retrosynthetic Analysis and Strategy Toward Antibiotic BE
43472B Total Synthesis of Antibiotic BE
43472B Conclusion GARSUBELLIN A Introduction Sibasaki and Kanai's Retrosynthetic Analysis and Strategy Shibasaki and Kanai's Total Synthesis Danishefsky's Retrosynthetic Analysis and Strategy Danishefsky's Total Synthesis Conclusion WELWITINDOLINONE A Introduction Baran's Retrosynthetic Analysis and Strategy Barans' Total Synthesis Wood's Retrosynthetic Analysis and Strategy Wood's Total Synthesis Conclusion IEJIMALIDE B Introduction Retrosynthetic Analysis and Strategy Total Synthesis Conclusion KEDARCIDIN CHROMOPHORE AND MADUROPEPTIN CHROMOPHORE Introduction Retrosynthetic Analysis and Strategy for Kedarcidin Chromophore Total Synthesis of Kedarcidin Chromophore Retrosynthetic Analysis and Strategy for Maduropeptin Chromophore Total Synthesis of Maduropeptin Chromophore Conclusion BIYOUYANAGIN A Introduction Retrosynthetic Analysis and Strategy Total Synthesis Conclusion AZADIRACHTIN Introduction Retrosynthetic Analysis and Strategy Synthesis Conclusion RESVERATROL
DERIVED NATURAL PRODUCTS Introduction Snyder's Retrosynthetic Analysis and Strategy for a Collection of Resveratrol
Derived Natural Products Snyder's Total Synthesis of a Collection of Resveratrol
Derived Natural Products Nicolaou and Chen's Retrosynthetic Analysis and Strategy for Hopeahainol A and Hopeanol Nicolaou and Chen's Total Synthesis of Hopeahainol A and Hopeanol Conclusion CHLOROSULFOLIPID CYTOTOXIN Introduction Retrosynthetic Analysis and Strategy Total Synthesis Conclusion SPOROLIDE B Introduction Retrosynthetic Analysis and Strategy Total Synthesis Conclusion 11,11'
DIDEOXYVERTICILLIN A AND CHAETOCIN Introduction Retrosynthetic Analysis and Strategy for 11,11'
Dideoxyverticillin A Total Synthesis of 11,11'
Dideoxyverticillin A Retrosynthetic Analysis and Strategy for Chaetocin Total Synthesis of Chaetocin Conclusion VANNUSAL B Introduction Retrosynthetic Analysis and Strategy Total Synthesis Conclusion HAPLOPHYTINE Introduction Fukuyama and Tokuyama's Retrosynthetic Analysis and Strategy Fukuyama and Tokuyama's Total Synthesis Nicolaou and Chen's Retrosynthetic Analysis and Strategy Nicolaou and Chen's Total Synthesis Conclusion PALAU'AMINE Introduction Retrosynthetic Analysis and Strategy Total Synthesis Conclusion
Rezensionen
?The present volume?and hopefully future books of this series?offer an exciting and outstanding overview of the subject of natural products total syntheses in its complexity and variety. Classics in Total Synthesis III will surely itself become a classic in the literature on the state of the art of contemporary organic synthetic chemistry.? ? Angewandte Chemie Int. Ed. 2011 "... a volume, (...) which any chemist with an interest in synthetic organic chemistry will wish to acquire." ?JACS (on a previous volume) "...this superb book (...) will be an essential purchase for many organic chemists." ?Nature (on a previous volume) "... One of my co-workers confessed that Classics I was the book on his bedside table while he prepared his thesis defense. Isn't that the highest distinction for a monograph?" ?Angewandte Chemie, 2004 (on a previous volume)
Nowadays, books that concentrate on the area of organic synthesis are numerous enough to fill whole inventories of libraries. But of that multitude, only a few books have been as outstanding in recent years as the series Classics in Total Synthesis, written by K. C. Nicolaou with various co-authors. This series can therefore already be justifiably called a classic in itself. Likewise, the third volume of this series, published by Wiley-VCH in February 2011, will surely continue the success of the previous volumes, and will certainly be a must-have in the libraries of synthetically orientated groups.
The concept of the preceding volumes has been closely retained. In 26 chapters, including an introductory chapter, syntheses of more than 40 natural products or natural product core structures are discussed in detail. The syntheses, together with historical excursions, have been taken from literature of the years 2003 to 2010. Each chapter begins with background information about the discovery, structure elucidation, and biological significance of the target molecule(s). To aid the reader_s orientation, key concepts of the total synthesis described are provided at the beginning of each chapter. After describing retrosyntheses that have been achieved, and any preliminary synthetic work, the chapter gives a very detailed description of the synthesis of the target structure, including almost all the individual steps. All literature references are clearly identified by chapter endnotes, thus allowing rapid access to the primary sources. The chapter ends with a short summary and a well-chosen, detailed, and extensive list of references. This alone is one of the great strengths of the book, and provides every synthetic chemist with an excellent pool for the solution of his or her own synthetic problems. Also particularly valuable for the reader are the short reviews on specific topics, which have the scope and style of review articles. Thus, one finds surveys on current topics of interest such as organocatalysis (Chapter 7: littoralisone, oseltamivir, hirsutellone B) and C_H activation (Chapter 2: tetrodotoxin) next to overviews of more classical themes such as Schenk ene reactions with singlet oxygen (Chapter 12: tetracycline), photochemically induced [2+2] cycloadditions (Chapter 18: biyouyanagin A), [2+2+2] cycloadditions, Diels-Alder reactions with o-quinones (Chapter 22: sporolid B), and Kagan-Molander SmI2 couplings (Chapter 24: vannusal B). The review of asymmetric halogenation reactions (Chapter 21: chlorosulfolipid cytotoxin) is particularly well-written, as it clearly demonstrates, to the young scientist as well as to the post- or pre-graduate student, that there are still enough chemical transformations that have not yet been sufficiently studied, and therefore leave room for personal creativity and ambition.
Novelties of this third volume compared to the previous ones are mainly concerned with the detailed contents. The depth of mechanistic discussions has been greatly increased. The introductions to the chapters often feature insights into the biosynthesis of the natural product concerned (e.g., Chapter 10: stephacidin). Some small sections describe problems associated with structure elucidation, which then led to revision of the supposed structure in the context of the total synthesis (e.g., in Chapter 4: azaspiracid-1). The very instructive concept of discussing and comparing several different syntheses of a target structure in a parallel fashion, which was introduced in the second volume of this series, has now been further developed in a clever way. Sometimes it would also have been useful for the synthetic chemist reader to be given an explanation of why a specific unusual reagent was chosen at a certain stage during the planning or carrying out of a synthesis, and why an apparently more convenient and conventional procedure was avoided. Such explanations, and possibly also descriptions of unsuccessful attempted routes, could give the reader an even more detailed insight into problems of reactivity or selectivity of a specific reagent or substrate.
The layout of this book has only been slightly changed compared with previous volumes. One innovation is the introduction of a colored title page at the beginning of each chapter, presenting an attractive graphical illustration of the target structure, together with its natural source and a picture of the leader of the group that worked on the total synthesis. However, the opportunity to similarly illustrate other parts of the chapter has not been taken; especially in the introduction, figures or graphics in color might have improved the accessibility of the contents. The question of whether it would be an advantage to also introduce color into the synthetic schemes depends on the reader_s personal taste as well as the costs of the book. On the other hand, the great success of this series does support a continuation of the style in its present form.
As the selection of synthetic target molecules for this book is exclusively taken from the more recent literature, in contrast to the first volume of the series, it remains to be seen whether the syntheses described will eventually become true classics. This book will certainly contribute its share to ensuring that these syntheses will be used as outstanding models for teaching and research purposes, even 20 or more years from now. One could also consider an even broader selection of target molecules and structures, which might be less close to the main author_s field of work and experience (at least 10 out of 26 chapters deal with the author_s syntheses). Indisputably, K. C. Nicolaou has made outstanding contributions in his research field. But who would not, for this very reason, like to see discussions of other scientists_ syntheses by the master himself?
A particularly extensive account is given in Chapter 3, which describes an impressive 60 g total synthesis of discodermolide by Novartis. This clearly demonstrates the increasing scientific, but also industrial, importance of complex syntheses of natural products. The present volume - and hopefully future books of this series - offer an exciting and outstanding overview of the subject of natural products total syntheses in its complexity and variety. Classics in Total Synthesis III will surely itself become a classic in the literature on the state of the art of contemporary organic synthetic chemistry.
Dirk Menche, Sebastian Essig
Organisch-Chemisches Institut
Ruprecht-Karls-Universität Heidelberg (Germany)
Angew. Chem. Int. Ed. 2011, 50, 5995 - 5996
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