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 language||English (US)|
|Number of pages||5|
|Journal||Journal of Organic Chemistry|
|State||Published - 1987|
ASJC Scopus subject areas
- Organic Chemistry