Synthesis of the oudemansins, naturally occurring β-methoxyacrylates from basidomycetes

Mark D. Wittman, James Kallmerten

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Abstract

Short, stereocontrolled syntheses of the antifungal metabolites oudemansins A (1) and B (2) from a common precursor (5) are described. Stereospecific olefination of 5 via the β-keto phosphine oxides 12 and 21 affords dienes (E)-7 and (E)-22, which are transformed to the corresponding styryl esters 14 and 23. Introduction of the β-methoxyacrylate group by acylation of 14 and 23 with N-formylimidazole affords the title compounds exclusively.

Original languageEnglish (US)
Pages (from-to)4303-4307
Number of pages5
JournalJournal of Organic Chemistry
Volume52
Issue number19
StatePublished - 1987

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ASJC Scopus subject areas

  • Organic Chemistry

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