Asymmetric total synthesis of pseurotin A

Yujiro Hayashi, Mitsuru Shoji, Shinpei Yamaguchi, Takasuke Mukaiyama, Junichiro Yamaguchi, Hideaki Kakeya, Hiroyuki Osada

Research output: Contribution to journalArticle

50 Citations (Scopus)

Abstract

(Matrix presented) The asymmetric total syntheses of pseurotin A and 8-O-demethylpseurotin A have been accomplished. Key reactions are a NaH-promoted intramolecular cyclization of an alkynylamide to form a γ-lactam, an aldol reaction of a benzylidene-substituted ketone, and the late-stage introduction of the benzoyl group by a selective oxidation of a benzylidene moiety with dimethyldioxirane (DMD).

Original languageEnglish
Pages (from-to)2287-2290
Number of pages4
JournalOrganic Letters
Volume5
Issue number13
DOIs
Publication statusPublished - 2003 Jun 26

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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    Hayashi, Y., Shoji, M., Yamaguchi, S., Mukaiyama, T., Yamaguchi, J., Kakeya, H., & Osada, H. (2003). Asymmetric total synthesis of pseurotin A. Organic Letters, 5(13), 2287-2290. https://doi.org/10.1021/ol034630s