Asymmetric total synthesis of (–)-rossinone A

Katsuya Saito, Kazuki Kurasawa, Chiaki Takino, Shigefumi Kuwahara, Masaru Enomoto

Research output: Contribution to journalArticlepeer-review

Abstract

The asymmetric total synthesis of (–)-rossinone A, a meroterpene exhibiting a range of pharmacologically important biological activities, has been accomplished for the first time from geraniol by a concise eight-step sequence that involves the Horner–Wadsworth–Emmons reaction of an aldehyde derived from a geranylated hydroquinone intermediate with a chiral phosphonate prepared via the highly diastereoselective Davis oxidation of a known oxazolidinone derivative.

Original languageEnglish
Article number153456
JournalTetrahedron Letters
Volume84
DOIs
Publication statusPublished - 2021 Nov 9

Keywords

  • Davis oxidation
  • Horner–Wadsworth–Emmons reaction
  • Meroterpene
  • Rossinone

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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