Abstract
Correlation of protolyofoligenic acid (II) with cycloartenol (III) was established to certify the stereostructure of II. Protolyofoligenic acid (II) was derived to 24, 25-di-O-isopropylidene-9 (10)-cyclolanostane-3α-ol (VIII) through protolyofoligenol (VI) and the corresponding aldehyde (VII). Cycloartenol (III) was acetylated, epoxidized, and benzoylated. The product, dibenzoate, was separated into 24R and 24S isomers by column and preparative thin-layer chromatography. Hydrolyzed product of 24R isomer, which has 3β-hydroxyl group, was derived to isopropylidene derivative, oxidized to 3-oxo compound and reduced by Meerwein-Ponndorf method to yield 3α-hydroxyl compound. The final product was identified with (VIII), which was derived from protolyofoligenic acid.
