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 - 2008
Externally publishedYes

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Pyrones
Cyclization
Biological Products
activity (biology)
Acids
routes
acids
synthesis
products

ASJC Scopus subject areas

  • Organic Chemistry
  • Physical and Theoretical Chemistry
  • Biochemistry
  • Molecular Medicine

Cite this

Rate-accelerating effect by the neighboring-group participation of protecting groups in the dehydrative cyclization of 1,3,5-triketones. / Sakakura, Akira; Watanabe, Hitoshi; Ishihara, Kazuaki.

In: Organic Letters, Vol. 10, No. 12, 2008, p. 2569-2572.

Research output: Contribution to journalArticle

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