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Communication | Special issue | Vol 59, No. 2, 2003, pp.445-451
Published online, 1st January, 1970
DOI: 10.3987/COM-02-S47
Trimethylaluminum-promoted 1,4-Addition Reaction of Cuprates to Six or Eight-membered 2-Hydroxymethyl Enones

Khanitha Pudhom, Jun-ichi Matsuo, and Teruaki Mukaiyama*

*The Kitasato Institute, Center for Basic Research, 6-15-5 (TCI), Toshima, Kita-ku, Tokyo 114-0003, Japan

Abstract

1,4-Addition reaction of higher order cyanocuprates such as Ph2Cu(CN)Li2 and [Et3SiO(CH2)3C(=CH2)]2Cu(CN)Li2 (3) to six or eight-membered cyclic 2-hydroxymethyl enones proceeded efficiently by successive treatment with trimethylaluminum and cuprate reagents. A side chain for C-ring of 19-hydroxypaclitaxel (1) was introduced in high yields on treating highly functionalized eight-membered cyclic hydroxymethyl enone (2c) with trimethylaluminum and cuprate (3).