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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.
List of contents
PREFACE
INTRODUCTION
Intermediate in the Total Synthesis of Brevetoxin A
THE INERTIA OF CONVENTIONAL FUNCTIONAL GROUPS
Welwitindolinone A Isonitrile
'Overprotecting-Maverick' Protecting Groups
THE DIELS - ALDER REACTION
(-)-Platensimycin 40
Stephacidins A and B 49
THE ALDOL CONDENSATION 61
The ABC Ring Moiety of (-)-Norzoanthamine
(+)-TMC-151C 71
CYCLIZATIONS: CONCERTED, RADICAL, OR POLAR?
(±)-Merrilactone A
(-)-Pseudolaric Acid B
Formal Synthesis of Platensimycin
MACROCYCLES: FROM RELUCTANT RING CLOSURE TO RELUCTANT RING OPENING
Ustiloxin D
Largazole
STEREOCHEMISTRY, CONTROLLED OR UNCONTROLLED?
(-)-Samaderin Y
(±)-Lyconadin A
Vannusal B
TRANSITION METAL-MEDIATED TRANSFORMATIONS VS 'CONVENTIONAL' REACTIONS
Blumiolide C
Arylomycin A2
(-)-Strychnine
WHEN METATHESIS FAILS
(+)-Saxitoxin
Laulimalide Family
OXIDATIONS IN C - C BOND BUILDING
Cortistatins A and J
Gambierol ABC Moiety
THE FAILURE OF EPOXIDE RING OPENING AND THE LIMITS OF CASCADE REACTIONS
C_D_E_F_ Domain of Maitotoxin
About the author
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).
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.
Report
"Like its predecessor, this book will interest advanced, research-oriented students, their mentors, and organic synthesis practitioners. Summing Up: Recommended. Upper-division undergraduates through professionals/practitioners." ( Choice , 1 January 2014)
