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 journalArticlepeer-review

32 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 languageEnglish
Pages (from-to)1820-1823
Number of pages4
JournalOrganic Letters
Volume13
Issue number7
DOIs
Publication statusPublished - 2011 Apr 1

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