Enantioselective synthesis of metacycloprodigiosin via the 'Wasserman pyrrole'

Marvin M. Vega, Diana M. Crain, Leah C. Konkol, Regan J. Thomson*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

6 Scopus citations

Abstract

Abstract A concise, nine-step enantioselective total synthesis of metacycloprodigiosin is reported. The synthesis provides increased step-efficiency over the previous racemic and enantioselective syntheses of this compound. Key features of the work include investigations into a convergent oxidative coupling reaction and subsequent ring-closing metathesis to deliver an advanced pyrrole intermediate we name the 'Wasserman pyrrole' that can be converted to metacycloprodigiosin in one step.

Original languageEnglish (US)
Article number45599
Pages (from-to)3228-3230
Number of pages3
JournalTetrahedron Letters
Volume56
Issue number23
DOIs
StatePublished - Jul 3 2015

Keywords

  • Metacycloprodigiosin
  • Oxidative coupling
  • Prodigiosin alkaloids
  • Ring-closing metathesis

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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