Formal total syntheses of (-)-isoavenaciolide and (-)-ethisolide from L-quebrachitol

Noritaka Chida, Takahiko Tobe, Masami Suwama, Masami Ohtsuka, Seiichiro Ogawa

Research output: Contribution to journalArticle

19 Citations (Scopus)

Abstract

The stereoselective conversions of the naturally occurring optically active cyclitol, L-quebrachitol 5, into the known synthetic intermediates, 3 and 4, for preparations of structurally interesting bislactones, (-)-isoavenaciolide 1 and (-)-ethisolide 2, respectively, are described. These bislactones, 3 and 4, were synthesized from the common intermediate 19, which was prepared by periodate oxidation of the bicyclic cyclitol derivative 17.

Original languageEnglish
Pages (from-to)2667-2673
Number of pages7
JournalJournal of the Chemical Society, Perkin Transactions 1
Issue number20
Publication statusPublished - 1992 Dec 1

ASJC Scopus subject areas

  • Chemistry(all)

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