Biosynthesis-inspired intramolecular oxa-conjugate cyclization of α,β-unsaturated thioesters: Stereoselective synthesis of 2,6-cis-substituted tetrahydropyrans

Haruhiko Fuwa; Kenkichi Noto; Makoto Sasaki

doi:10.1021/ol200333p

Biosynthesis-inspired intramolecular oxa-conjugate cyclization of α,β-unsaturated thioesters: Stereoselective synthesis of 2,6-cis-substituted tetrahydropyrans

Haruhiko Fuwa, Kenkichi Noto, Makoto Sasaki

Research output: Contribution to journal › Article › peer-review

27 Citations (Scopus)

Abstract

Intramolecular oxa-conjugate cyclization of α,β-unsaturated thioesters under Brønsted acid catalysis, inspired by biosynthesis of polyketide natural products, provides a variety of 2,6-cis-substituted tetrahydropyran derivatives with excellent diastereoselectivities. An added bonus of this methodology is that the product tetrahydropyrans could be readily elaborated to various derivatives by exploiting the unique reactivity of the thioester group.

Original language	English
Pages (from-to)	1820-1823
Number of pages	4
Journal	Organic letters
Volume	13
Issue number	7
DOIs	https://doi.org/10.1021/ol200333p
Publication status	Published - 2011 Apr 1

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol200333p

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AU - Sasaki, Makoto

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Biosynthesis-inspired intramolecular oxa-conjugate cyclization of α,β-unsaturated thioesters: Stereoselective synthesis of 2,6-cis-substituted tetrahydropyrans

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