Enantioselective total synthesis of (-)-minovincine in nine chemical steps: An approach to ketone activation in cascade catalysis

Brian N. Laforteza, Mark Pickworth, David W.C. MacMillan

Research output: Contribution to journalArticle

48 Scopus citations

Abstract

Dressed to the nines: The first enantioselective total synthesis of (-)-minovincine has been accomplished in nine chemical steps and 13 % overall yield. A novel, one-step Diels-Alder/β-elimination/conjugate addition organocascade sequence allowed rapid access to the central tetracyclic core in an asymmetric manner. Boc=tert-butoxycarbonyl, LG=leaving group, PMB=para-methoxybenzyl.

Original languageEnglish (US)
Pages (from-to)11269-11272
Number of pages4
JournalAngewandte Chemie - International Edition
Volume52
Issue number43
DOIs
StatePublished - Oct 18 2013

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)

Keywords

  • alkaloids
  • enantioselectivity
  • natural products
  • organocatalysis
  • total synthesis

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