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[1] : pbk ISBN 9783527292318
内容説明
K.C. Nicolaou - Winner of the Nemitsas Prize 2014 in Chemistry
This book is a must for every synthetic chemist. With didactic skill and clarity, K. C. Nicolaou and E. Sorensen present the most remarkable and ingenious total syntheses from outstanding synthetic organic chemists.
To make the complex strategies more accessible, especially to the novice, each total synthesis is analyzed retrosynthetically. The authors then carefully explain each synthetic step and give hints on alternative methods and potential pitfalls. Numerous references to useful reviews and the original literature make this book an indispensable source of further information.
Special emphasis is placed on the skillful use of graphics and schemes: Retrosynthetic analyses, reaction sequences, and stereochemically crucial steps are presented in boxed sections within the text. For easy reference, key intermediates are also shown in the margins.
Graduate students and researchers alike will find this book a gold mine of useful information essential for their daily work. Every synthetic organic chemist will want to have a copy on his or her desk.
目次
Constructing the Molecules of Nature
Strychnine (Woodward)
Strychnine (Overman)
Penicillin V (Sheehan)
Reserpine (Woodward)
Vitamin B12 (Woodward)
Progesterone (Johnson)
Prostaglandins F2-alpha and E2 (Corey)
Prostaglandins A2 and F2-alpha (Stork)
Carpanone (Chapman)
Monensin (Kishi)
Monensin (Still)
Biotin (Baggiolini)
Periplanone B (Still)
Periplanone B (Schreiber)
Isocomene (Pirrung)
Estrone (Vollhardt)
Erythronolide B (Corey)
Endiandric Acids A-G (Nicolaou)
Thienamycin (Merck)
Asteltoxin (Schreiber)
Amphotericin B (Nicolaou)
L-Hexoses (Masamune & Sharpless)
Cytovaricin (Evans)
Indolizamycin (Danishefsky)
Ginkgolide B (Corey)
Paoniflorigenin and Paoniflorin (Corey)
Methyl homosecodaphniphyllate (Heathcock)
Gilvocarcin M and V (Suzuki)
Calicheamicin gamma-1I (Nicolaou)
Taxol (Nicolaou)
Rapamycin (Nicolaou)
Menthol (Noyori)
Palytoxin (Kishi)
Brevetoxin B (Nicolaou)
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[1] : hardcover ISBN 9783527292844
内容説明
K. C. Nicolaou, E. J. Sorensen Classics in Total Synthesis Targets, Strategies, Methods This book is a must for every synthetic organic chemist. With didactic skill and clarity, K. C. Nicolaou and E. J. Sorensen present the most remarkable and ingenious total syntheses from the laboratories of some of the world's greatest synthetic organic chemists. To make the strategies more understandable and accessible, especially to the novice, each total synthesis is first analyzed retrosynthetically. The authors then carefully describe each step and comment on alternative methods and potential pitfalls. When appropriate, key chemical reactions are discussed in the wider context of the chemical literature, giving the reader a lesson in both total synthesis and synthetic methods. Diverse structural types of natural products and important organic transformations including pericyclic, ionic, radical, and photochemical reactions are covered. Catalysis, asymmetric synthesis, organometallic chemistry, and cyclization reactions are especially highlighted. Mechanism, reactivity, selectivity, and stereochemistry are presented clearly and discussed analytically.
Numerous references to useful reviews and the original literature will make this book the first point of entry into the vast field of synthetic organic chemistry. Special emphasis is placed on the skillful use of graphics and schemes. Retrosynthetic analyses, reaction sequences and crucial synthetic steps are presented in boxed, blue background sections within the text. For easy reference, key intermediates are also shown in the margins. Graduate students, teachers, and researchers alike will find this book to be a gold mine of useful information. Every synthetic chemist will have a copy on his or her desk.
目次
- Constructing the molecules of nature
- strychnine
- penicillin
- reserpine
- prostaglandin F2a and E2
- progesterone
- carpanone
- Vitamin B12
- prostaglandin A2 and F2a
- estrone
- erythronolide B
- monensin
- periplanone B
- isocomene
- monensin
- thienamycin
- endiandric acids
- biotin
- L-hexoses
- asteltoxin
- periplanone B
- menthol
- amphoteronolide B and amphotericin B
- ginkgolide B
- methyl homosecodaphniphllate
- indolizomycin
- cytovaricin
- gilvocarcin M and V
- rapamycin
- paeoniflorigenin and paeoniflorin
- strychnine
- taxol
- zaragozic acid A / squalestatin S1
- palytoxin
- brevetoxin B. (Part contents).
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2 : pbk ISBN 9783527306848
内容説明
Classics in Total Synthesis II is the long awaited sequel to Classics in Total Synthesis, a book that has made its mark as a superb tool for educating students and practitioners alike in the art of organic synthesis since its introduction in 1996. In this highly welcomed new volume, K. C. Nicolaou and Scott A. Snyder discuss in detail the most impressive accomplishments in natural product total synthesis during the 1990s and the first years of the 21st century. While all of the features that made the first volume of Classics so popular and unique as a teaching tool have been maintained, in this new treatise the authors seek to present the latest techniques and advances in organic synthesis as they beautifully describe the works of some of the most renowned synthetic organic chemists of our time.
* domino reactions, cascade sequences, biomimetic strategies, and asymmetric catalysis are systematically developed through the chosen synthesis
* cutting edge synthetic technologies are discussed in terms of mechanism and scope
* new reactions, such as olefin metathesis, are presented in mini-review style
* abundant references are given for further reading
Graduate students, educators, and researchers in the fields of synthetic and medicinal chemistry will wish to have a copy of this book in their collection as an indispensable companion that both augments and supplements the original Classics in Total Synthesis.
From reviews of "Classics in Total Synthesis":
"... a volume, (..) which any chemist with an interest in synthetic organic chemistry will wish to acquire."
JACS
"...this superb book (..) will be an essential purchase for many organic chemists."
Nature
目次
Introduction
Isochrysohermidin (Boger)
Swinholide A (Paterson)
Dynemicin A (Myers)
Ecteinascidin 743 (Corey)
Resiniferatoxin (Wender)
Epothilone A (Nicolaou)
Manzamine A (Winkler/Martin)
Vancomycin (Nicolaou/Evans)
Everninomicin 13,384-1 (Nicolaou)
Bisorbicillinoids (Nicolaou)
Aspidophytine (Corey)
CP-Molecules (Nicolaou)
Colombiasin A (Nicolaou)
Quinine (Stork)
Longithorone A (Shair)
FR-182877 (Sorensen)
Vinblastine (Fukuyama)
Quarigemine C and Psycholeine (Overman)
Diazonamide A (Nicolaou)
Plicamine (Ley)
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2 : hardcover ISBN 9783527306855
内容説明
This is the long awaited sequel to "Classics in Total Synthesis", a book that has made its mark as a superb tool for educating students and practitioners alike in the art of organic synthesis since its introduction in 1996. In this highly welcomed new volume, K. C. Nicolaou and Scott A. Snyder discuss in detail the most impressive accomplishments in natural product total synthesis during the 1990s and the first years of the 21st century. While all of the features that made the first volume of "Classics" so popular and unique as a teaching tool have been maintained, in this new treatise the authors seek to present the latest techniques and advances in organic synthesis as they beautifully describe the works of some of the most renowned synthetic organic chemists of our time.This book: Develops domino reactions, cascade sequences, biomimetic strategies, and asymmetric catalysis are systematically through the chosen synthesis; discusses the latest synthetic technologies in terms of mechanism and scope; includes new reactions, such as olefin metathesis, in mini-review style; abundant references for further reading; and, a CD with useful teaching material for lecturers is included with hardback version.
Graduate students, educators, and researchers in the fields of synthetic and medicinal chemistry will wish to have a copy of this book in their collection as an indispensable companion that both augments and supplements the original "Classics in Total Synthesis". From reviews of "Classics in Total Synthesis": '...a volume, .. which any chemist with an interest in synthetic organic chemistry will wish to acquire' - "JACS". '...this superb book.. will be an essential purchase for many organic chemists' - "Nature".
目次
Chapter 1. Introduction: Perspectives in Total Synthesis.Chapter 2. Isochrysohermidin (D.L. Boger).Chapter 3. Swinholide A (I. Paterson).Chapter 4. Dynemicin A (A.G. Myers and S.J. Danishefsky).Chapter 5. Ecteinascidin 743 (E.J. Corey).Chapter 6. Resiniferatoxin (P.A. Wender).Chapter 7. Epothilones A and B (K.C. Nicolaou).Chapter 8. Manzamine A (J.D. Winkler and S.F. Martin).Chapter 9. Vancomycin (K.C. Nicolaou and D.A. Evans).Chapter 10. Everninomicin 13,384-1 (K.C. Nicolaou).Chapter 11. Bisorbicillinoids (K.C. Nicolaou).Chapter 12. Aspidophytine (E.J. Corey).Chapter 13. CP-Molecules (K.C. Nicolaou).Chapter 14. Colombiasin A (K.C. Nicolaou).Chapter 15. Quinine (G. Stork).Chapter 16. Longithorone A (M.D. Shair).Chapter 17. (--)-FR182877 (E.J. Sorensen).Chapter 18. Vinblastine (T. Fukuyama).Chapter 19. Quadrigemine C and Psycholeine (L.E. Overman).Chapter 20. Diazonamide A (K.C. Nicolaou).Chapter 21. Plicamine (S.V. Ley).Chapter 22. Okaramine N (E.J. Corey).Author Index.Subject Index.
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3 : softcover ISBN 9783527329571
内容説明
K.C. Nicolaou - Winner of the Nemitsas Prize 2014 in Chemistry
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.
目次
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 (R)), AND HIRSUTELLONE B
Introduction
Introduction to Littoralisone
Total Synthesis of Littoralisone
Introduction to Oseltamivir (Tamiflu (R))
Total Synthesis of Oseltamivir (Tamiflu (R))
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
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3 : hardcover ISBN 9783527329588
内容説明
K.C. Nicolaou - Winner of the Nemitsas Prize 2014 in Chemistry
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.
目次
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 (R)), AND HIRSUTELLONE B
Introduction
Introduction to Littoralisone
Total Synthesis of Littoralisone
Introduction to Oseltamivir (Tamiflu (R))
Total Synthesis of Oseltamivir (Tamiflu (R))
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
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