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Paper | Regular issue | Vol 53, No. 12, 2000, pp.2759-2768
Published online, 1st January, 1970
DOI: 10.3987/COM-00-9061
■ High Regio- and Stereoselectivity in Facile One-Pot Conversion of Taxoids to the Primary Alcohols: Precursors for the Synthesis of 4-Deacetoxypacilitaxel and Analogues

Qian Cheng, Tohru Horiguchi, Marina Yamaguchi, and Takayuki Oritani*

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

Abstract

The conversion of alkali metal hydroxy base sensitive taxoids bearing ester groups to the corresponding primary alcohols in a facile one-pot protocol has been reported. This process which involves two steps of hydroboration and oxidation, using a mixture of NMO and TBHP (2:1), which possesses high regio- and stereoselectivity was first established. Proof of the chemistry used in the preparation of a precursor for the synthesis of a 4-deacetoxypaclitaxel analogue has also been presented.