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Communication

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

Supporting Info

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

Abstract

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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Communication

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

Abstract

Available Supporting Information for This Article

PDF

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SciFinder Links

History

Recommend & Share

Related Content

Enantioselective Synthesis of (+)-Cephalostatin 1

Chemical and Biological Studies of Nakiterpiosin and Nakiterpiosinone

Enantioselective C−C Bond Formation by Rhodium-Catalyzed Tandem Ylide Formation/[2,3]-Sigmatropic Rearrangement between Donor/Acceptor Carbenoids and Allylic Alcohols

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