An enantiocontrolled entry to the tricyclic polar segment of (+)-fusarisetin A

Aki Kohyama, Naoki Kanoh, Eunsang Kwon, Yoshiharu Iwabuchi

Research output: Contribution to journalArticlepeer-review

7 Citations (Scopus)

Abstract

The tricyclic polar segment of fusarisetin A, designed for preparing analogues for structure-activity relationship studies of the aliphatic segment thereof, has been constructed in an enantiocontrolled manner, featuring the Yamamoto asymmetric epoxidation of a homoallylic alcohol, C3-selective ring-opening of a 3,4-epoxy alcohol, stereocontrolled merger of a γ-lactone with Garner's counterpart, and ruthenium-catalyzed ring-closing metathesis.

Original languageEnglish
Pages (from-to)517-519
Number of pages3
JournalTetrahedron Letters
Volume57
Issue number5
DOIs
Publication statusPublished - 2016 Feb 3

Keywords

  • Epoxide ring opening
  • Fusarisetin A
  • Oxidative lactonization
  • Yamamoto asymmetric epoxidation

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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