The Logic of Chemical Synthesis [Paperback]

E. J. Corey (Author), Xue-Min Cheng (Author)

Book Description

ISBN-10: 0471115940 | ISBN-13: 978-0471115946 | Publication Date: June 29, 1995 | Edition: 1

The Logic of Chemical Synthesis The title of this three-part volume derives from a key theme of the book-the logic underlying the rational analysis of complex synthetic problems. Although the book deals almost exclusively with molecules of biological origin, which are ideal for developing the fundamental ideas of multistep synthetic design because of their architectural complexity and variety, the approach taken is fully applicable to other types of carbon-based structures. Part One outlines the basic concepts of retrosynthetic analysis and the general strategies for generating possible synthetic pathways by logical reduction of molecular complexity. Systematic retrosynthetic analysis and the concurrent use of multiple independent strategies to guide problem solving greatly simplify the task of devising a new synthesis. This way of thinking has been used for more than two decades by one of the authors to teach the analysis of difficult synthetic problems to many hundreds of chemists. A substantial fraction of the intricate syntheses which have appeared in the literature in recent years have been produced by these individuals and their students. Part Two, a collection of multistep syntheses, provides much integrated information on synthetic methods and pathways for the construction of interesting target molecules. These syntheses are the result of synthetic planning which was based on the general principles summarized in Part One. Thus, Part Two serves to supplement Part One with emphasis on the reactions of synthesis and on specific examples of retrosynthetically planned syntheses. Part Three is intended to balance the coverage of Parts One and Two and to serve as a convenient guide to the now enormous literature of multistep synthesis. Information on more than six hundred interesting multistep syntheses of biologically derived molecules is included. It is hoped that the structural range and variety of target molecules presented in Part Three will appeal to many chemists.

Editorial Reviews

From the Back Cover

The Logic of Chemical Synthesis The title of this three-part volume derives from a key theme of the book-the logic underlying the rational analysis of complex synthetic problems. Although the book deals almost exclusively with molecules of biological origin, which are ideal for developing the fundamental ideas of multistep synthetic design because of their architectural complexity and variety, the approach taken is fully applicable to other types of carbon-based structures. Part One outlines the basic concepts of retrosynthetic analysis and the general strategies for generating possible synthetic pathways by logical reduction of molecular complexity. Systematic retrosynthetic analysis and the concurrent use of multiple independent strategies to guide problem solving greatly simplify the task of devising a new synthesis. This way of thinking has been used for more than two decades by one of the authors to teach the analysis of difficult synthetic problems to many hundreds of chemists. A substantial fraction of the intricate syntheses which have appeared in the literature in recent years have been produced by these individuals and their students. Part Two, a collection of multistep syntheses, provides much integrated information on synthetic methods and pathways for the construction of interesting target molecules. These syntheses are the result of synthetic planning which was based on the general principles summarized in Part One. Thus, Part Two serves to supplement Part One with emphasis on the reactions of synthesis and on specific examples of retrosynthetically planned syntheses. Part Three is intended to balance the coverage of Parts One and Two and to serve as a convenient guide to the now enormous literature of multistep synthesis. Information on more than six hundred interesting multistep syntheses of biologically derived molecules is included. It is hoped that the structural range and variety of target molecules presented in Part Three will appeal to many chemists.

About the Author

ELIAS JAMES COREY, winner of the 1990 Nobel Prize in Chemistry, is Sheldon Emery Professor in the Department of Chemistry at Harvard University. XUE-MIN CHENG is a Research Associate specializing in cardiovascular medicinal chemistry at Parke-Davis/Warner-Lambert Company.

Product Details

• Paperback: 436 pages
• Publisher: Wiley-Interscience; 1 edition (June 29, 1995)
• Language: English
• ISBN-10: 0471115940
• ISBN-13: 978-0471115946
• Product Dimensions: 9.9 x 7 x 0.8 inches
• Shipping Weight: 1.9 pounds (View shipping rates and policies)
• Average Customer Review: 4.6 out of 5 stars  See all reviews (8 customer reviews)
• Amazon Best Sellers Rank: #341,830 in Books (See Top 100 in Books)
  • #6 in Books > Professional & Technical > Professional Science > Chemistry > Organic > Synthesis

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Customer Reviews

Most Helpful Customer Reviews

24 of 27 people found the following review helpful:

4.0 out of 5 stars Not a text for beginners, March 14, 2001

By 

Ray Frazier - See all my reviews

This review is from: The Logic of Chemical Synthesis (Paperback)

This text is a wonderful insight into the mind and chemical synthetic strategies of E. J. Corey. However, it is really not a good tool for beginning students. The sections on synthons and retrosnthetic strategies are fairly useful for beginners, but the majority of the text are the examples of total syntheses from Corey's work. While these are greatly useful as an insight into Corey and complex synthesis, it is not the best book for beginning students. Too often the routes Corey uses/used involve rare and expensive reagents, seldom the first choice in most labs. Students who start with this text are often confused when approaching a problem in a more realistic (cost concerned) environment and are confused as to what should be the first attempt at a particular transformation--Corey often tells what worked without mentioning what else was tried first, suggesting to the beginning student that the route ultimately used was the first choice, which often is not the case. Long story short, for advanced students or professors of chemistry this is an ideal text, but it is not something a beginning graduate student wants to study without a great deal of other sources.

7 of 7 people found the following review helpful:

5.0 out of 5 stars Logic Of Organic Synthesis, February 12, 2002

By 

Matthew M. Yau "Voracious reader" (San Francisco, CA) - See all my reviews
(REAL NAME)   

This review is from: The Logic of Chemical Synthesis (Paperback)

Organic chemists and practicing researchers would agree that this book goes hand-in-hand with Nicoloau's Classics in Total Synthesis. While the latter discusses the total synthesis of some of the most fascinating molecules from all over the world, The Logic of Chemical Synthesis is a collection of E. J. Corey's (winner of 1990 Nobel Prize in Chemistry) total syntheses. The book deals almost exclusively with molecules of biological origin.

Part 1 of the book discusses the basic concepts of retrosynthetic analysis. Subtopics include transform-based strategies, structure-based strategies, topological strategies, stereochemical strategies, functional group-based strategies, and convergence of such strategies. Many examples are provided to illustrate these strategies. Molecules shown include Longifolene, Porantherine, Gibberellic acid, Picrotoxinin, and Ginkgolide B. The strategies help generate possible synthetic pathways by logical reduction of molecular complexity. In more plain words, the section help dissect complex molecules and reduce them into smaller precursors.

Part 2 focuses on how to apply the synthesis strategies from Part 1 in synthetic methods and pathways for the construction of many complex target molecules. The syntheses combine general principles presented in Part 1 and further enforces idea of retrosynthetic analysis by showing specific examples and emphasizing on reactions of synthesis. The section breaks down into macrocyclic structures, heterocyclic structures, sesquiterpenoids, polycyclic isoprenoids, prostanoids, and Leukotrienes. The syntheses presented here might be somewhat more difficult to comprehend at first sight. E. J. Corey here presents the straightforward synthesis of molecules without any didactic explanations and comments. Unlike the Nicoloau approach in Classics in Total Synthesis, retrosynthetic analysis of these complex targeting molecules is omitted. The book also skips all the reaction intermediates and reaction mechanisms. A good way to understand the syntheses would be to go backward and make sense out of each step.

Part 3 deals with current chemical literature pertaining to multistep syntheses. The book assumes knowledge of at least one course in organic syntheses which emphasize on synthetic strategies and named reactions.

4 of 6 people found the following review helpful:

5.0 out of 5 stars A masterpiece in the realm of synthetic chemistry books, July 4, 2000

By 

Carlos Valdez (Frederick, Maryland) - See all my reviews

This review is from: The Logic of Chemical Synthesis (Paperback)

This is an extraordinarily well-written book which may be used as a learning tool for the starting Organic synthetic chemist, who, with no doubt, will enjoy himself by going through it. Many references are given after each synthesis, so that the reader can refer to specific journals and find out the actual reaction conditions that were carried out for each synthesis. Also, at the end of the book, a list of several natural products and their classical preparations are given with their respective journal citation. I believe that this book provides the organic syntehtic chemist with a feel for the area and its boundless applications and limits. I would recommend this book to anybody engaged in some kind of synthetic work, since there is good chance that this book will have the answer to some of their questions.