Protective Groups in Organic Synthesis, 3rd Edition

American Journal of Pharmaceutical Education, Spring 2000 by Gibbs, Richard A

THEODORA W GREENE AND PETER G. M. WUTS. Protective Groups in Organic Synthesis, 3rd Edition. New York, NY.Y John Wiley & Sons, Inc., 1999. xxi 779 pp., I fig., 2 tbls. $84.95.

The proper employment of protective groups is crucial to the synthesis of almost any medicinally important natural product, and many "non-natural" drug candidates as well. The previous two editions of this book are concise guides to protective groups, including information on their introduction, selective removal, and stability. As such, they are exceptionally valuable resources for the practicing synthetic medicinal chemist. A key and invaluable portion of the book are the novel reactivity charts (presented in Chapter 10 of the 3rd edition). These charts indicate at a glance, in a general manner, the stability of numerous protective groups under a variety of synthetic conditions.

The 3rd edition of this now-classic reference extends and enhances its utility, both quantitatively and qualitatively. In quantitative terms, the 3rd edition is 306 pages longer than the second edition, with 2349 new citations and the inclusion of 348 new protective groups. This quantitative augmentation of the book is impressive and significant, and alone would provide justification for the publication of this new edition. Equally significant, however, is the qualitative enhancement of the 3rd edition with the addition of entirely new and novel information. Specifically, two new chapters have been added to the previous ones on protective groups for phenols and hydroxyl, carbonyl, carboxyl, thiol and amino groups. Chapters 8 and 9 describe protective groups for the alkyne -CH moiety and for the phosphate groups. The latter chapter is certain to be of particular interest to medicinal chemists, with the vital, central, and increasing importance of phosphorus chemistry in biological settings.

The second edition of this book has been one of the most useful books on my personal reference shelf. I am sure that the 3rd edition will prove to be even more useful. It should be in the library at every institution where synthetic chemistry is done, and I strongly recommend it for the bookshelf of every synthetic medicinal chemist.

Richard A. Gibbs Wayne State University