Abstract
The synthesis and biological activity of (±)-pyrenolide B (1) and related compounds are described. The known (Z)-2-decen-9-olide (7) prepared via decan-9-olide (6) from 2-ethoxycarbonylcyclononanone (4) was converted to 9 by the deconjugative process, which, upon oxidation with m-chloroperbenzoic acid, led to the epoxy lactone 10. Base-promoted epoxide ring opening of 10 and subsequent oxidation furnished keto lactone 8, which, on treatment with phenylselenenyl chloride and subsequent oxidative elimination, provided (±)-pyrenolide B (1). The antimicrobial activity of (±)-1, 6, 7, 8, 9, 10a, 10b and 11a was examined against fungi and yeast.
