Substrate-Controlled Stereoselective
Synthesis of Ophiocerin C

Jhillu S. Yadav; N. Rami Reddy; B. Bala Murali Krishna; Ch. Vijaya Vardhan; Basi V. Subba Reddy

doi:10.1055/s-0029-1218708

PAPER

Substrate-Controlled Stereoselective Synthesis of Ophiocerin C

Jhillu S. Yadav*, N. Rami Reddy, B. Bala Murali Krishna, Ch. Vijaya Vardhan, Basi V. Subba Reddy
Division of Organic Chemistry-I, Indian Institute of Chemical Technology, Hyderabad 500007, India
Fax: +91(40)27160512; e-Mail: yadavpub@iict.res.in;

Abstract

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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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References

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