ROLLINONE, A REVISION AND EXTENSION OF STRUCTURE

The structure of rollinone [2] has been revised according to recently acquired 2D-nmr data. Instead of the previously reported terminal γ-methylbutyrolactone and 14-keto moieties, rollinone [2] was found to contain a butyrolactone between C-1 and C-4 with a pendant acetylmethyl moiety at C-2. The relative stereochemistry between C-15 and C-24 in rollinone [2] was established as erythro-cis-threo-cis-threo (or threo-cis-threo-cis-erythro) by1H-nmr experiments using the diacetate derivative. The structure was confirmed via chemical conversion of 25-desoxy-4-hydroxyneorollinicin [1] into 2. © 1990, American Chemical Society. All rights reserved.