Absolute configuration of (+)-aureothin: A toxic metabolite possessing γ-pyrone unit

Y. Ishibashi, S. Ohba, S. Nishiyama, S. Yamamura

Research output: Contribution to journalArticle

18 Citations (Scopus)

Abstract

The absolute configuration of aureothin (1) has been determined by synthesis of (-)-aureonone (4) bearing R-configuration. X-Ray single crystallographic analysis of 21 guaranteed the stereochemistry of the chiral center introduced by Sharpless asymmetric epoxidation, as well as that of isoaureothin (3) which was previously synthesized in a similar pathway. Aureothin (1) itself was also synthesized, although Wittig coupling reaction of 4 under basic conditions, caused a partial epimerization of the chiral center.

Original languageEnglish
Pages (from-to)3643-3649
Number of pages7
JournalBulletin of the Chemical Society of Japan
Volume68
Issue number12
DOIs
Publication statusPublished - 1995 Dec 1

ASJC Scopus subject areas

  • Chemistry(all)

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