Stereoselective synthesis of malyngic acid and fulgidic acid

Yusuke Kurashina, Ayako Miura, Masaru Enomoto, Shigefumi Kuwahara

Research output: Contribution to journalArticle

14 Citations (Scopus)

Abstract

A new stereoselective total synthesis of malyngic acid has been achieved from a known oxazolidinone derivative via eight steps involving the Evans asymmetric alkylation as the chirality-inducing step and chelation-controlled Zn(BH4)2 reduction of an α-hydroxy ketone intermediate for the installation of the 12,13-anti stereochemistry. Fulgidic acid, the C12-epimer of malyngic acid, has also been synthesized in eight steps from the same starting material by using syn-selective K-Selectride reduction of an α-alkoxy ketone intermediate.

Original languageEnglish
Pages (from-to)1649-1653
Number of pages5
JournalTetrahedron
Volume67
Issue number9
DOIs
Publication statusPublished - 2011 Mar 4

Keywords

  • Diastereoselective reduction
  • Fulgidic acid
  • Malyngic acid
  • Oxylipin
  • Total synthesis

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Fingerprint Dive into the research topics of 'Stereoselective synthesis of malyngic acid and fulgidic acid'. Together they form a unique fingerprint.

  • Cite this