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Note | Regular issue | Vol 53, No. 7, 2000, pp.1579-1582
Published online, 1st January, 1970
DOI: 10.3987/COM-00-8914
A Convenient Method for the Synthesis of C-10 Alkylated Docetaxel Analogs Using Tris-(trimethylsilyl)silane as a Radical Mediator

Shin Iimura, Satoru Ohsuki, Kouichi Uoto, Kiyoshi Nakayama, Hirofumi Terasawa, and Tsunehiko Soga*

*New Product Research Laboratories IV, Daiichi Pharmaceutical Co., Ltd., 1-16-13, Kitakasai, Edogawa, Tokyo 134-8630, Japan


Radical coupling has been investigated as a method for preparing Docetaxel analogs substituted at the C-10 position. C-10-Xanthate derivatives of 7-O-TES-10-deacetylbaccatin III were coupled with acrolein using organosilanes as radical mediators. Among the organosilanes that were investigated, tris(trimethylsilyl)silane gave the best results. This method provides C-10 alkylated baccatin III in good yield, and avoids the use of potentially toxic tributyltin hydride.