A concise total synthesis of biologically active frutinones via tributylphosphine-catalyzed tandem acyl transfer-cyclization

Masahito Yoshida, Koya Saito, Yuta Fujino, Takayuki Doi

Research output: Contribution to journalArticlepeer-review

21 Citations (Scopus)

Abstract

A concise and step-economical total synthesis of biologically active frutinones has been achieved. Tributylphosphine (PBu3) efficiently induced the tandem acyl transfer-cyclization of carbonates 5 to afford 3-methoxycarbonylflavone derivatives 4 in excellent yields. Finally, concomitant deprotection and lactonization under acidic conditions furnished the desired frutinones A (1a), B (1b), and the proposed structure of frutinone C (1c).

Original languageEnglish
Pages (from-to)3452-3458
Number of pages7
JournalTetrahedron
Volume70
Issue number21
DOIs
Publication statusPublished - 2014 May 27

Keywords

  • Flavone
  • Organocatalyst
  • Regioselective
  • Tandem reaction
  • Total synthesis

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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