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, Jon T. Njardarson

Research output: Contribution to journalArticle

47 Scopus citations

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.

Original languageEnglish (US)
Pages (from-to)2768-2769
Number of pages2
JournalJournal of the American Chemical Society
Volume129
Issue number10
DOIs
StatePublished - Mar 14 2007
Externally publishedYes

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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