Highly Selective Copper-Catalyzed Ring Expansion of Vinyl Thiiranes:  Application to Synthesis of Biotin and the Heterocyclic Core of Plavix

Erik Rogers, Hiroshi Araki, Lindsay A. Batory, Christine E. McInnis, and Jon T. Njardarson*
Department of Chemistry and Chemical Biology, Baker Laboratory, Cornell University, Ithaca, New York 14853-1301
J. Am. Chem. Soc., 2007, 129 (10), pp 2768–2769
DOI: 10.1021/ja069059h
Publication Date (Web): February 16, 2007
Copyright © 2007 American Chemical Society
, *

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Abstract

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We report herein a new, highly selective, mild copper-catalyzed vinyl thiirane ring-expansion protocol for the formation of 2,5-dihydrothiophenes. Preliminary substrate scope and applications of this new synthetic disconnection to the formal racemic total synthesis of biotin and the synthesis of the antiplatelet blockbuster pharmaceutical agent Plavix are described.

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History

  • Published In Issue March 14, 2007
  • Received December 18, 2006

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