Efficient route to functionalized eight-membered lactones based on intramolecular silicon-directed acylative ring-opening reactions of 3- (Tetrahydro-2-furyl)propanoic acid derivatives

Ohi Hidenori, Susumu Inoue, Yoshiharu Iwabuchi, Hiroshi Irie, Susumi Hatakeyama

Research output: Contribution to journalArticlepeer-review

Abstract

Exposure of 3-(tetrahydro-2-furyl)-3-trimethylsilylpropanoic acids and 3-(2-trimethylsilylmethyltetrahydro-2-furyl)propanoic acids to trifluoroacetic anhydride allows intramolecular acylative ring-opening reaction to give the corresponding eight-membered lactones in moderate to good yields.

Original languageEnglish
Pages (from-to)1757-1759
Number of pages3
JournalSynlett
Issue number11
Publication statusPublished - 1999 Jan 1
Externally publishedYes

Keywords

  • Acyloxonium ion
  • Eight-membered lactones
  • Octalactin analogs
  • Ring enlargement
  • Silicon compounds

ASJC Scopus subject areas

  • Organic Chemistry

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