Protective Groups in Organic Synthesis 3rd Ed - Greene - Wiley 1999.pdf - Chemia - Triteleia

Protective Groups in Organic Synthesis, Third Edition. Theodora W. Greene, Peter G.M. Wuts

1999 John Wiley & Sons, Inc.

ISBNs: 0-471-16019-9 (Hardback); 0-471-22057-4 (Electronic)

PROTECTIVE GROUPS IN

ORGANIC SYNTHESIS

THIRD EDITION

Theodora W. Greene

The Rowland Institute for Science

and

Peter G. M. Wuts

Pharmacia and Upjohn Company

A WILEY-INTERSCIENCE PUBLICATION

JOHN WlLEY & SONS, INC.

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PREFACE TO THE THIRD

EDITION

Organic synthesis has not yet matured to the point where protective groups are

not needed for the synthesis of natural and unnatural products; thus, the develop-

ment of new methods for functional group protection and deprotection conti-

nues. The new methods added to this edition come from both electronic searches

and a manual examination of all the primary journals through the end of 1997.

We have found that electronic searches of Chemical Abstracts fail to find many

new methods that are developed during the course of a synthesis, and issues of

selectivity are often not addressed. As with the second edition, we have

attempted to highlight unusual and potentially useful examples of selectivity for

both protection and deprotection. In some areas the methods listed may seem

rather redundant, such as the numerous methods for THP protection and depro-

tection, but we have included them in an effort to be exhaustive in coverage. For

comparison, the first edition of this book contains about 1500 references and 500

protective groups, the second edition introduces an additional 1500 references

and 206 new protective groups, and the third edition adds 2349 new citations and

348 new protective groups.

Two new sections on the protection of phosphates and the alkyne-CH are

included. All other sections of the book have been expanded, some more than

others. The section on the protection of alcohols has increased substantially,

reflecting the trend of the nineties to synthesize acetate-and propionate-derived

natural products. An effort was made to include many more enzymatic methods

of protection and deprotection. Most of these are associated with the protection

of alcohols as esters and the protection of carboxylic acids. Here we have not

attempted to be exhaustive, but hopefully, a sufficient number of cases are pro-

vided that illustrate the true power of this technology, so that the reader will

examine some of the excellent monographs and review articles cited in the refer-

ences. The Reactivity Charts in Chapter 10 are identical to those in the first

edition. The chart number appears beside the name of each protective group

when it is first introduced. No attempt was made to update these Charts, not only

because of the sheer magnitude of the task, but because it is nearly impossible in

Vi PREFACE

a two-dimensional table to address adequately the effect that electronic and

steric controlling elements have on a particular instance of protection or depro-

tection. The concept of fuzzy sets as outlined by Lofti Zadeh would be ideally

suited for such a task.

The completion of this project was aided by the contributions of a number of

people. I am grateful to Rein Virkhaus and Gary Callen, who for many years for-

warded me references when they found them, to Jed Fisher for the information

he contributed on phosphate protection, and to Todd Nelson for providing me a

preprint of his excellent review article on the deprotection of silyl ethers. I

heartily thank Theo Greene for checking and rechecking the manuscript-all 15

cm of it-for soelline and consistencv and for the arduous task of checking all

the references for accuracy. I thank Fred Greene for reading the manuscript, for

his contribution to Chapter 1 on the use of protective groups in the synthesis of

. .

himastatin, and for his-contribution to the introduction to Chapter 9, on phos-

phates. I thank my wife, Lizzie, for encouraging me to undertake the third edi-

tion, for the hours she spent in the library looking up and photocopying hundreds

of references, and for her understanding while I sat in front of the computer night

after night and numerous weekends over a two-year period. She is the greatest!

Kaiarnoroo. Michigan

June 1998

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