Rate-accelerating effect by the neighboring-group participation of protecting groups in the dehydrative cyclization of 1,3,5-triketones

Akira Sakakura, Hitoshi Watanabe, Kazuaki Ishihara

Research output: Contribution to journalArticle

15 Citations (Scopus)

Abstract

(Chemical Equation Presented) Neighboring-group participation of an acyl protecting group efficiently promotes the Brønsted acid-catalyzed dehydrative cyclization of 1,3,5-triketones to γ-pyrones, whereas a bulky silyloxy group in the β-position retards the cyclization. This reaction provides an efficient synthetic route for a common intermediate for the synthesis of γ-pyrone-containing bioactive natural products.

Original languageEnglish
Pages (from-to)2569-2572
Number of pages4
JournalOrganic Letters
Volume10
Issue number12
DOIs
Publication statusPublished - Dec 1 2008
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Fingerprint Dive into the research topics of 'Rate-accelerating effect by the neighboring-group participation of protecting groups in the dehydrative cyclization of 1,3,5-triketones'. Together they form a unique fingerprint.

  • Cite this