Synthesis and structural revision of phomopsin B, a novel polyketide carrying a 10-membered cyclic-ether ring

Yuko Izuchi, Hiroyuki Koshino, Yayoi Hongo, Nobuhiro Kanomata, Shunya Takahashi

Research output: Contribution to journalArticle

12 Citations (Scopus)

Abstract

Total synthesis of the proposed structure 2 for phomopsin B was achieved by using an intramolecular olefin metathesis as a key step. The spectral data, however, did not match with those of the natural product reported. Re-examination of the reported NMR data led to the structural revision of phomopsin B to known dothiorelone A 18. The R configuration of dothiorelone A was determined by total synthesis through a cross-metathesis with a chiral olefin 19.

Original languageEnglish
Pages (from-to)3360-3363
Number of pages4
JournalOrganic Letters
Volume13
Issue number13
DOIs
Publication statusPublished - 2011 Jul 1

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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