Title: More dead ends and detours : en route to successful total synthesis /
Authors: Sierra, Miguel A.,; Torre, María C. de la,; Cossío, Fernando P.,
Year: 2013
Subjects: Organic compounds Synthesis
Abstract: 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: The Inertia of Conventional Functional Groups -- The Diels-Alder Reaction -- The Aldol Condensation -- Cyclizations: Concerted, Radical, or Polar? -- 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 -- The Failure of Epoxide Ring Opening and the Limits of Cascade Reactions.