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.

PREFACE INTRODUCTIONIntermediate 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 40Stephacidins A and B 49THE ALDOL CONDENSATION 61The ABC Ring Moiety of (-)-Norzoanthamine (+)-TMC-151C 71CYCLIZATIONS: 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