Substrate-Controlled Stereoselective Synthesis of Ophiocerin C

Abstract

A novel stereoselective total synthesis of ophiocerin C was accomplished starting from l-(+)-tartaric acid. The C3,C4 vic-diol moiety was obtained from tartaric acid, and the stereogenic centre at C6 was created by substrate-controlled epoxidation and subsequent regioselective cleavage of the epoxide ring.

Key words

Wittig reactions - tartaric acid - epoxidations - ring opening - ophiocerin C - stereoselective synthesis

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