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Synthesis 2010(10): 1621-1624
DOI: 10.1055/s-0029-1218708
DOI: 10.1055/s-0029-1218708
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New YorkSubstrate-Controlled Stereoselective Synthesis of Ophiocerin C
Further Information
Received
1 February 2010
Publication Date:
24 March 2010 (online)
Publication History
Publication Date:
24 March 2010 (online)

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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