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Letters in Organic Chemistry

Editor-in-Chief

ISSN (Print): 1570-1786
ISSN (Online): 1875-6255

Evaluation of Sulfonamides in the Protection of Phenylisoserine for the Semisynthesis of Taxol®

Author(s): Peter G.M. Wuts, Rui L. Gu and Jill M. Northuis

Volume 1, Issue 4, 2004

Page: [372 - 375] Pages: 4

DOI: 10.2174/1570178043400587

Price: $65

Abstract

The 4-nitrophenylsulfonyl, the benzothiazolsulfonyl and the anthracenesulfonyl protecting groups were evaluated in the protection of the phenylisoserine side chain, as part of a semisynthesis of paclitaxel. The mechanism for the cleavage of the anthracenesulfonyl group using thiols was also examined, and found to proceed by an addition elimination pathway, which is in contrast to the reported reductive mechanism. The use of the siamyldimethylsilyl group for protection of baccatin III is discussed and compared with the triethylsilyl group.

Keywords: 4-nitrophenylsulfonamide, benzothiazolsulfonamide and the anthracenesulfonamide, taxol, paclitaxel


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