Nine-step enantioselective total synthesis of (-)-vincorine

Benjamin D. Horning, David W.C. MacMillan

Research output: Contribution to journalArticle

121 Scopus citations

Abstract

A concise and highly enantioselective total synthesis of the akuammiline alkaloid (-)-vincorine has been accomplished. A key element of the synthesis is a stereoselective organocatalytic Diels-Alder, iminium cyclization cascade sequence, which serves to construct the tetracyclic alkaloid core architecture in one step from simple achiral precursors. The challenging seven-membered azepanyl ring system is installed by way of a single electron-mediated cyclization event initiated from an acyl telluride precursor. The total synthesis of (-)-vincorine is achieved in nine steps and 9% overall yield from commercially available starting materials.

Original languageEnglish (US)
Pages (from-to)6442-6445
Number of pages4
JournalJournal of the American Chemical Society
Volume135
Issue number17
DOIs
StatePublished - May 1 2013

All Science Journal Classification (ASJC) codes

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

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