Synlett 2010(3): 457-461  
DOI: 10.1055/s-0029-1219191
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Stereoselective Total Synthesis of (-)-Ovalicin

J. S. Yadav*, P. Narayana Reddy, B. 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;
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Publikationsverlauf

Received 28 August 2009
Publikationsdatum:
11. Januar 2010 (online)

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Abstract

A new synthetic route for epoxyketone 3 is described, which is a key intermediate in Barton’s synthesis of ovalicin (1), a powerful anti-angiogenetic inhibitor, from commercially available d-ribose. The key reactions involved in this synthesis are ring-closing metathesis, Rubottom oxidation and Corey-Chaykovsky epoxidation. The subsequent transformations are carried out according to Barton’s strategy to complete the total synthesis of (-)-ovalicin.