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Communication | Special issue | Vol 13, No. 1, 1979, pp.151-156
Published online, 1st January, 1970
DOI: 10.3987/S-1979-01-0151
Synthesis of Bicyclic Coriolin Models

Hisanobu Hashimoto, Toshio Ito, Haruhisa Shirahama, and Takeshi Matsumoto*

*Faculty of Science, Hokkaido University, Kita 10 Nishi 8, Kita-ku, Sapporo, Hokkaido 060-0810, Japan

Abstract

Bicyclic coriolin models 10a and 13 have been obtained in a stereoselective manner from 3, through methylenation at C-4, epoxidation at the C-1 double bond, borohydride reduction and subsequent epoxidation at the methylene group. Similar transformation of 16b, obtained from the enol acetate of 3 through oxidation (mCPBA), afforded dihydroxydiepoxide 23, Jones oxidation of which gave a bicyclic diketocoriolin B model 26.