Catalytic asymmetric synthesis of both syn- and anti-3,5-dihydroxy esters: Application to 1,3-polyol/α-pyrone natural product synthesis

Shin Ya Tosaki, Tetsuhiro Nemoto, Takashi Ohshima, Masakatsu Shibasaki

Research output: Contribution to journalArticle

56 Citations (Scopus)

Abstract

(Matrix presented) We describe a catalytic asymmetric synthesis of both syn- and anti-3,5-dihydroxy esters. The method relies upon catalytic asymmetric epoxidation of α,β-unsaturated imidazolides and amides, using lanthanide-BINOL complexes, and diastereoselective reduction of ketones. The method was applied to the enantioselective syntheses of 1,3-polyol/α -pyrone natural products 9a, 9b, and strictifolione (10). The absolute stereochemistry of 9a and 9b was also determined.

Original languageEnglish
Pages (from-to)495-498
Number of pages4
JournalOrganic Letters
Volume5
Issue number4
DOIs
Publication statusPublished - Feb 20 2003
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Molecular Medicine

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