Utilisation of L-quebrachitol in natural product synthesis. Total synthesis and absolute configuration of (-)-oudemansin X

Noritaka Chida, Ken Yamada, Seiichiro Ogawa

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Abstract

The stereoselective conversion of the naturally occurring optically active cyclitol, L-quebrachitol 2, into antifungal β-methoxyacrylate, oudemansin X 1 is described. This first total synthesis of 1 fully confirmed the proposed absolute configuration of the antibiotic and showed the importance of 2 as a versatile chiral starting material in natural product syntheses.

Original languageEnglish
Pages (from-to)1957-1962
Number of pages6
JournalJournal of the Chemical Society, Perkin Transactions 1
Issue number17
Publication statusPublished - 1993 Dec 1

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ASJC Scopus subject areas

  • Chemistry(all)

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