More Dead Ends and Detours
En Route to Successful Total Synthesis
1. Edition May 2013
288 Pages, Softcover
A must-have textbook for master's and PhD students in organic chemistry and researchers in the pharmaceutical industry who want to improve their own chemical reaction planning to succeed in natural product total synthesis.
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.
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
Stephacidins A and B 49
THE ALDOL CONDENSATION 61
The ABC Ring Moiety of (-)-Norzoanthamine
CYCLIZATIONS: CONCERTED, RADICAL, OR POLAR?
(-)-Pseudolaric Acid B
Formal Synthesis of Platensimycin
MACROCYCLES: FROM RELUCTANT RING CLOSURE TO RELUCTANT RING OPENING
STEREOCHEMISTRY, CONTROLLED OR UNCONTROLLED?
TRANSITION METAL-MEDIATED TRANSFORMATIONS VS 'CONVENTIONAL' REACTIONS
WHEN METATHESIS FAILS
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
Maria C. de la Torre studied chemistry at the Universidad Complutense de Madrid (UCM) where she received her PhD in 1986. After a postdoctoral stay at Imperial College under Steven Ley and Colorado State University under Albert Meyers, she returned to Madrid in
1989 as a scientific researcher at the Consejo Superior de Investigaciones Científicas. At present she is a staff member of the Synthesis, Structure and Properties of Organic Compounds Department, at the Instituto de Química Orgánica General (IQOG). Her current
research interests focus on the chemistry of densely functionalized natural products, the preparation of natural product hybrids with mixed and/or complementary biological properties, and the development of synthetic strategies to the building of metal-based natural product macrocycles.
Fernando P. Cossío studied Chemical Science at the University of Zaragoza and went on to receive a PhD in 1986 at the University of the Basque Country (UPV/EHU). He has spent post-doctoral fellowships at the Centre National de la Recherche Scientifique under
Dr. Jean-Paul Picard in Talence (France) and at the University of California Los Angeles under Kendall N. Houk. He became an Associate Professor at the UPV/EHU Faculty of Chemistry in 1988 and a full Professor of this University in 2002. He has occupied a number
of posts, such as the dean of the UPV/EHU Faculty of Chemistry, vice-chancellor of Research and International Relations at the UPV/EHU (2001-2004), and president of the Executive Committee of Ikerbasque, the Basque foundation for science (2009-). His current
research interests focus on the study of pericyclic and C-C bond forming reactions by computational and experimental methods.