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Paper | Special issue | Vol 59, No. 2, 2003, pp.595-604
Published online, 1st January, 1970
DOI: 10.3987/COM-02-S58
Stereoselective Synthesis of the Optically Pure AB-Ring Moiety of Trichothecene Sesquiterpene (+)-Calonectrin

Akira Iida, Kazuhide Konishi, Hironobu Matsumoto, Masafumi Kaneko, and Kiyoshi Tomioka*

*Graduate School of Pharmaceutical Sciences, Kyoto University, 46-29 Yoshida-shimoadachi-machi, Sakyo-ku, Kyoto 606-8501, Japan

Abstract

The optically pure trichothecene cis-AB ring moiety (1) was synthesized starting from an optically pure butenolide (7) through the ring closing olefin metathesis for the formation of the A-ring and a Lewis acid mediated cyclization to the cis-fused tetrahedrochromane skeleton that had been converted to natural trichothecene, (+)-calonectrin.