Dead Ends and Detours Direct Ways to Successful Total Synthesis

by Sierra, Miguel A.; de la Torre, Maria C.; Nicolaou, K. C.

• ISBN13: 9783527306442
• ISBN10: 3527306447
• Edition: 1st
• Format: Paperback
• Copyright: 2004-12-27
• Publisher: Wiley-VCH

Summary

Based on a review in the Angewandte Chemie, which was one of the journals top ten articles, Dead Ends and Detours: Direct Ways to Successful Total Synthesis focuses on problems that arise when implementation of the syntheses lead to deep changes in the original planning; the thought-process involved to solve these problems; and the advance in knowledge derived these experiences.

Author Biography

Miguel A. Sierra studied chemistry at the UCM (Madrid), receiving his PhD in 1987, after which he was appointed Assistant Professor. After a postdoctoral stay at Colorado State University (Professor Louis Hegedus), he returned to Madrid where he was became Professor in 1990. His research encompasses the development of new processes based on transition-metal complexes, the preparation of new bioorganometallic compounds tailor-made for specific applications in crop protection, and the study of environmental organic processes. Professor Sierra is the secretary of the Madrid regional division of the Spanish Chemical Society and a member of the Scientific Advisory Board for the Organization for the Prohibition of Chemical Weapons (OPCW). <br> Maria C. de la Torre studied chemistry at the Universidad Complutense de Madrid (UCM) where she received her PhD in 1986. After postdoctoral work at Imperial College (under Professor Steven Ley) and Colorado State University (Professor Albert Meyers), she returned to Madrid in 1989 as a scientific researcher at the Consejo Superior de Investigaciones Cientfficas. Her current research interests focus on the chemistry of densely functionalized natural products, and the preparation of natural product hybrids with mixed and/or complementary biological properties.<br>

Table of Contents

Foreword.

Preface.

Abbreviations.

Chapter 1: Introduction: From the Paper to the Laboratory.

References.

Chapter 2: Tuning-up, Tactical and Strategic Changes.

2.1 Tuning-up Reaction Conditions.

2.2 Tactical Changes.

2.3 Strategic Changes.

References.

Chapter 3: Working with Models.

3.1 (–)-Stenine.

3.2 (+)-Piperazinomycin.

3.3 (+)-Damavaricin D.

3.4 Dynemicin A.

References.

Chapter 4: The Unexpected Reactivity or Inertia of Common Functional Groups.

4.1 Pseudotabersonine.

4.2 Octalactins A and B.

4.3 (–)-Polycavernoside A.

References.

Chapter 5: The Influence of Remote Substituents.

5.1 “Alive” Dead Steric Volume.

5.2 The Reactive Remote Group.

References.

Chapter 6: The Elusive Side Chain.

6.1 (±)-Scopadulcic Acid B.

6.2 Dysidiolide.

6.3 (+)-Epoxydictymene.

6.4 (±)-Lepadiformine.

References.

Chapter 7: The Unpredictable Stereochemistry.

7.1 Nocardiones A and B.

7.2 (±)-Breynolide.

7.3 Hamigerans A and B.

7.4 Calphostin A.

7.5 Fragment C3-C10 of Cytovaricin.

7.6 Goniocin.

References.

Chapter 8: Reluctant Ring Closures.

8.1 Discorhabdin C.

8.2 Discorhabdin A.

8.3 Frondosin B.

8.4 (–)-Laulimalide.

8.5 ent-Rubifolide.

8.6 Roseophilin Tricyclic Core: The Formal Total Synthesis of Roseophilin.

8.7 (–)-Papuamine.

References.

Subject Index.