The chemistry of the taxane diterpene: Stereoselective synthesis of 10-deacetoxy-11,12-epoxypaclitaxel

Geraldine C.B. Harriman, Ravi K. Jalluri, Gary L. Granewald, David G. Vander Velde, Gunda I. Georg, Richard H. Himes

Research output: Contribution to journalArticlepeer-review

9 Scopus citations

Abstract

Epoxidation of the olefin in 10-deacetoxybaccatin III (6) and 10-deacetoxypaclitaxel (9) was accomplished with meta-chloroperbenzoic acid leading to a novel pentacyclic ring system. Hydroxyl directed delivery of the epoxidizing agent did not appear to play a role in the stereoselectivity of the reaction as epoxidation occurred at the β-face of the molecule. 10-Deacetoxy-11,12-epoxypaclitaxel (10) proved to be more active than paclitaxel (1) in the microtubule assembly assay and three-fold less cytotoxic than paclitaxel against B16 melanoma cells.

Original languageEnglish (US)
Pages (from-to)8909-8912
Number of pages4
JournalTetrahedron Letters
Volume36
Issue number49
DOIs
StatePublished - Dec 4 1995

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