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

doi:10.1021/ol800860p

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 journal › Article › peer-review

17 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 language	English
Pages (from-to)	2569-2572
Number of pages	4
Journal	Organic Letters
Volume	10
Issue number	12
DOIs	https://doi.org/10.1021/ol800860p
Publication status	Published - 2008
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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year = "2008",

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AU - Watanabe, Hitoshi

AU - Ishihara, Kazuaki

PY - 2008

Y1 - 2008

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AB - (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.

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

Abstract

ASJC Scopus subject areas

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