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Paper | Regular issue | Vol 53, No. 12, 2000, pp.2629-2642
Published online, 1st January, 1970
DOI: 10.3987/COM-00-8929
Chemical Oxidation of Taxoids with m-CPBA and Dimethyl Dioxirane: Regioselective Epoxidation of Taxinine J Derivatives

Tohru Horiguchi, Masanori Nagura, Qian Cheng, Takayuki Oritani,* and Toshio Kudo

*Laboratory of Applied Bioorganic Chemistry, Division of Life Science, Graduate School of Agricultural Science, Tohoku University, 1-1 Tsutsumidori-Amamiyamachi, Aoba-ku, Sendai 981-8555, Japan

Abstract

Epoxidation of taxinine J derivative (2c) with m-CPBA afforded a mixture of 4 Éø,20-epoxide (3), 4Éø,20 : 11β,12β-diepoxide (4) and 11 β,12β-epoxide (5). The proportion of the yields was dependent on temperature (3 : 4 = 80 : 10 at room temperature, 4 : 5 = 68 : 25 at 0-10°C). The reactions of derivatives of taxinine (2b) with m-CPBA and dimethyldioxirane (DMDO) were also investigated.