More dead ends and detours : en route to successful total synthesis / Miguel A. Sierra, Maria C. de la Torre, and Fernando P. Cossio.

Format:

Book

Author/Creator:

Sierra, Miguel A.

Contributor:

Cossío, Fernando P.

Torre, María C. de la.

Language:

English

Subjects (All):

Organic compounds--Synthesis.

Organic compounds.

Physical Description:

1 online resource (xxi, 266 p.) : ill.

Edition:

1st ed.

Place of Publication:

Weinheim an der Bergstrasse, Germany : Wiley-VCH Verlag GmbH, c2013.

Summary:

Success comes in many forms and in synthesis it can be a failure that results in their ultimate successful solutions. This long-awaited sequel to "Dead Ends and Detours" retains the proven concept while featuring over 20 new case studies of failed strategies and their (successful) solutions in natural product total synthesis. Additionally, computational models are used to discuss the problem in much more detail and to provide readers with additional information not found in the primary literature. The topics range from classic synthetic reactions (e.g. Diels Alder reaction), metal-mediated coupling reactions, metathesis, and asymmetric catalysis to the importance of protecting and activating groups. This book will benefit not only graduate students in organic chemistry but also advanced researchers as they gain knowledge derived from the step-by-step analysis of mistakes made in the past and, thus be able to improve their own chemical reaction planning. With its coverage of the most commonly applied reaction types, the book perfectly complements its predecessor, which focuses on general aspects, such as reactivity and selectivity.

Contents:

Intro

Related Titles

Title Page

Copyright

Dedication

Foreword

Acknowledgment

Preface

Abbreviations and Acronyms

1: Introduction

Section 1.1 Synthesis of an intermediate in the total synthesis of brevetoxin A

1.1 Intermediate in the Total Synthesis of Brevetoxin A [16]

References

2: The Inertia of Conventional Functional Groups

2.1 Welwitindolinone A Isonitrile [1]

2.2 "Overprotecting-Maverick" Protecting Groups

3: The Diels-Alder Reaction

3.1 (−)-Platensimycin [2]

3.2 Stephacidins A and B [13]

: The Aldol Condensation

4.1 The ABC Ring Moiety of (−)-Norzoanthamine [1]

4.2 (+)-TMC-151C [15]

5: Cyclizations: Concerted, Radical, or Polar?

5.1 (±)-Merrilactone A [3]

5.2 (−)-Pseudolaric Acid B [14]

5.3 Formal Synthesis of Platensimycin [28]

6: Macrocycles: from Reluctant Ring Closure to Reluctant Ring Opening

6.1 Ustiloxin D [2]

6.2 Largazole [10]

7: Stereochemistry, Controlled or Uncontrolled?

7.1 (−)-Samaderin Y [3]

7.2 (±)-Lyconadin A [10]

7.3 Vannusal B [21]

8: Transition Metal-Mediated Transformations vs "Conventional" Reactions

8.1 Blumiolide C [5]

8.2 Arylomycin A2 [17]

8.3 (−)-Strychnine [30]

9: When Metathesis Fails

9.1 (+)-Saxitoxin [6]

9.2 Laulimalide Family [19]

10: Oxidations in C-C Bond Building

10.1 Cortistatins A and J [2]

10.2 Gambierol ABC Moiety [9]

11: The Failure of Epoxide Ring Opening and the Limits of Cascade Reactions

11.1 C'D'E'F' Domain of Maitotoxin

Index.

Notes:

Includes bibliographical references at the end of each chapters and index.

Description based on online resource; title from title page (ebrary, viewed August 5, 2013).

Description based on publisher supplied metadata and other sources.

ISBN:

3-527-65464-X

3-527-65465-8

3-527-65462-3

OCLC:

846849851