Organic Synthesis via Examination of Selected Natural Products

Annotation This book is written for advanced graduate and undergraduate students to expose them to a variety of strategies for the synthesis of organic compounds. This is done largely within the context of natural products synthesis, but some unnatural products synthesis is also included. Multiple approaches to each group of synthesis targets are presented, and the approaches are compared with one another with an eye on similarities and differences. General problems in organic synthesis (for example, strategies for the preparation of 6-membered rings and 5-membered rings, the importance of oxidation state, the problem of acyclic diastereoselectivity, the problem of controlling absolute stereochemistry, the importance of functional group relationships) are introduced early in the book and revisited throughout the text within the context of a variety of structurally unrelated natural products. The book provides readers with a somewhat historical overview of organic and natural products chemistry, and spans synthetic methodology that dates from the 1940's to the present time. It is written in a style that readers will find entertaining at times. It also contains lots of useful references with complete titles provided Front Matter ......Page 1 Introduction ......Page 11 Steroids ......Page 24 Prostaglandins ......Page 78 Pyrrolizidine Alkaloids ......Page 142 Juvabione and the Vicinal Stereochemistry Problem ......Page 159 Functional Group Reactivity Patterns and Difunctional Relationships ......Page 206 Some Unnatural Products — Twistane and Triquinacene ......Page 246 Alkaloids — Difunctional Relationships and the Importance of the Mannich Reaction ......Page 278 Alkaloids from “Dart-Poison” Frogs ......Page 333 Morphine and Oxidative Phenolic Coupling ......Page 400 Olefin Synthesis and Cecropia Juvenile Hormone ......Page 441 A Recent Example of Structure Determination Through Total Synthesis and Convergent Syntheses: Lasonolide A ......Page 474 Ionophores: Calcimycin ......Page 496 Erythromycin A Aglycone ......Page 526 Back Matter ......Page 548 Complete with problems and solutions, this book is written for advanced graduate and undergraduate students to expose them to a variety of strategies for the synthesis of organic compounds. This is done largely within the context of natural products synthesis, but includes some unnatural products synthesis. Multiple approaches to each group of synthesis targets are presented, and the approaches are compared with one another with an eye on similarities and differences. General problems in organic synthesis (for example, strategies for the preparation of 6-membered rings and 5-membered rings, th Suitable for advanced graduate and undergraduate students, this book intends to expose them to a variety of strategies for the synthesis of organic compounds. It presents multiple approaches to each group of synthesis targets, and compares the approaches with one another with an eye on similarities and differences.