Asymmetric total synthesis of enantiopure (-)-methyl jasmonate via catalytic asymmetric intramolecular cyclopropanation of α-diazo-β-keto sulfone

Hiroyuki Takeda, Hideaki Watanabe, Masahisa Nakada

Research output: Contribution to journalArticle

35 Citations (Scopus)

Abstract

A new asymmetric total synthesis of enantiopure (-)-methyl jasmonate is described. This synthesis was accomplished starting from the new enantiopure building block prepared via the catalytic asymmetric intramolecular cyclopropanation (IMCP) of the α-diazo-β-keto 1-naphthyl sulfone, which was devised to give good selectivity both in the IMCP reaction and in the C-alkynylation of the intermediate required for the total synthesis of enantiopure (-)-methyl jasmonate.

Original languageEnglish
Pages (from-to)8054-8063
Number of pages10
JournalTetrahedron
Volume62
Issue number34
DOIs
Publication statusPublished - 2006 Aug 21

Keywords

  • Catalytic asymmetric synthesis
  • Chiral building blocks
  • Intramolecular cyclopropanation
  • Total synthesis

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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