Preparation of novel synthons, uniquely functionalized tetrahydrofuran and tetrahydropyran derivatives

Masahisa Nakada, Masashi Takano, Yukitaka Iwata

Research output: Contribution to journalArticlepeer-review

3 Citations (Scopus)

Abstract

The dianion of the acetoacetic ester reacts with epibromohydrin derivatives to afford a mixture of (Z)-2-alkoxycarbonylmethylidenetetrahydrofuran derivative and (E)-2-alkoxycarbonylmethylidenetetrahydropyran derivative. The selective formation of the tetrahydrofuran derivative is achieved by the use of LiCIO4 as the additive. The preparation of the optically active tetrahydrofuran derivatives and tetrahydropyran derivatives is also examined, and the optical purity and absolute configuration of the products is elucidated.

Original languageEnglish
Pages (from-to)1581-1585
Number of pages5
JournalChemical and Pharmaceutical Bulletin
Volume48
Issue number10
DOIs
Publication statusPublished - 2000

Keywords

  • Acetoacetic ester
  • Dianion
  • Epibromohydrin
  • Epoxide
  • Tetrahydrofuran
  • Tetrahydropyran

ASJC Scopus subject areas

  • Chemistry(all)
  • Drug Discovery

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