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Nicolaou, K. C.; Chen, Jason S.

Classics in Total Synthesis 3 Further Targets, Strategies, Methods (Gebundene Ausgabe)

Wiley VCH Verlag GmbH, Wiley-VCH Verlag GmbH & Co. KGaA, Februar 2011


746 S. - Sprache: Englisch - 258x201x35 mm

ISBN: 3527329587 EAN: 9783527329588

Retaining his excellent, proven approach, world-famous chemist and passionate teacher K.C. Nicolaou compiles here the important strategies and tools employed to construct complex molecules. For a total of 42 syntheses of 25 challenging natural products he explains all the key steps of the synthetic pathway, highlighting the major developments in blue-boxed sections for easier understanding, and contrasting these to other synthetic methods. Similar to its predecessors and completing the trilogy, this textbook analyzes the syntheses in a didactic manner, with several chapters including mini-reviews of key methodologies, and an emphasis on the history, mechanism, scope, and generality of the reactions. In contrast to the first two volumes, this new one features full-color frontispieces. A wonderful tool for learning and teaching and a must-have for all current and future organic and biochemists.


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Inhaltsverzeichnis

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

Über den Autor

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.

Kritikerstimmen

?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)


ISBN 3-527-32958-7

ISBN 978-3-527-32958-8

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