Enantioselective total synthesis of enokipodins A-D, antimicrobial sesquiterpenes produced by the mushroom, Flammulina velutipes

Mana Saito, Shigefumi Kuwahara

Research output: Contribution to journalArticlepeer-review

25 Citations (Scopus)

Abstract

The first enantioselective total synthesis of enokipodins A, B, C and D, highly oxidized α-cuparenone-type sesquiterpenoids possessing antimicrobial activity, was accomplished in 8-28% overall yields from methyl (2,5-dimethoxy-4-methylphenyl)acetate by applying Meyers' diastereoselective alkylation protocol for the construction of their C7-quaternary asymmetric center. The present synthesis confirmed the absolute configuration of the enokipodins, and also constitutes a formal enantioselective synthesis of (S)-1,4-cuparenediol and (S)-cuparene-1,4-quinone.

Original languageEnglish
Pages (from-to)374-381
Number of pages8
JournalBioscience, Biotechnology and Biochemistry
Volume69
Issue number2
DOIs
Publication statusPublished - 2005 Feb

Keywords

  • Antibiotic
  • Cuparene
  • Enokipodin
  • Terpenoid

ASJC Scopus subject areas

  • Biotechnology
  • Analytical Chemistry
  • Biochemistry
  • Applied Microbiology and Biotechnology
  • Molecular Biology
  • Organic Chemistry

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