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Semisynthesis of Some 7-Deoxypaclitaxel Analogs from Taxine B
Peter H. G. Wiegerinck1, Lizette Fluks, Jeannet B. Hammink
1Department of Organic Chemistry, University of Nijmegen, NSR-Center, Toernooiveld, 6525 ED Nijmegen, The Netherlands.
The Journal of Organic Chemistry
|October 4, 1996
Abstract:
Taxine B (3), isolated from the dried needles of Taxus baccata, was converted into six novel 7-deoxypaclitaxel analogs, 20, 21a,b, and 23-25, that have structural changes at C1, C2, and C4. A method for the introduction of the benzoyl function at C2, via a benzylidene acetal at C1-C2, will be revealed. All compounds showed very little or no measurable cytotoxic activity against some well-characterized human tumor cell lines, probably due to the nonacylated hydroxyl group at C4.