Nine-step enantioselective total synthesis of (+)-minfiensine

Spencer B. Jones, Bryon Simmons, David W.C. MacMillan

Research output: Contribution to journalArticle

268 Scopus citations

Abstract

(Chemical Equation Presented) An enantioselective total synthesis of the Strychnos alkaloid (+)-minfiensine has been accomplished. Prominent features of this synthesis include (i) a new enantioselective organocatalytic Diels-Alder/amine cyclization sequence to build the central tetracyclic pyrroloindoline framework in four steps from commercial materials and (ii) a 6-exo-dig radical cyclization to forge the final piperidinyl ring system. This total synthesis of (+)-minfiensine was completed in nine chemical steps and 21% overall yield.

Original languageEnglish (US)
Pages (from-to)13606-13607
Number of pages2
JournalJournal of the American Chemical Society
Volume131
Issue number38
DOIs
StatePublished - 2009

All Science Journal Classification (ASJC) codes

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

Fingerprint Dive into the research topics of 'Nine-step enantioselective total synthesis of (+)-minfiensine'. Together they form a unique fingerprint.

  • Cite this