Catalytic iron-mediated ene carbocyclizations of trienes: enantioselective syntheses of the iridoid monoterpenes (-)-mitsugashiwalactone and (+)-isoiridomyrmecin

James M. Takacs, Young Chan Myoung

Research output: Contribution to journalArticle

53 Scopus citations

Abstract

The iron-catalyzed cycloisomerization of a chiral (2E,7E) 2,7,9-decatriene derivative bearing a methyl substituent adjacent to the 1,3-diene subunit proceeds with high levels of 1,2-stereoinduction relative to the resident methyl-bearing stereocenter. The stereochemistry of the chiral cyclopentane product is proven by conversion to (-)-Mitsugashiwalactone (1) and to (+)-Isoiridomyrmecin (2).

Original languageEnglish (US)
Pages (from-to)317-320
Number of pages4
JournalTetrahedron Letters
Volume33
Issue number3
DOIs
StatePublished - Jan 14 1992

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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