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Synfacts 2007(8): 0787-0787  
DOI: 10.1055/s-2007-968711
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Formal Synthesis of Biotin

Contributor(s): Philip Kocienski
E. Rogers, H. Araki, L. A. Batory, C. E. McInnis, J. T. Njardarson*
Cornell University, Ithaca, USA
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Publication History

Publication Date:
24 July 2007 (online)

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Significance

A new synthesis of dihydrothio­phenes entails the Cu(II)-catalyzed ring expansion of vinyl thiiranes at elevated temperature. The reaction was used to synthesize intermediate F in a previous synthesis of biotin and intermediate J, a component of Plavix. Ten further examples were reported with yields ranging from 35-95%.