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The absolute configuration of the branched methyl group in ante-iso type side chain moiety on the long chain base of glucocerebroside, HLC-2-A, which was isolated from the sea cucumber Holothuria leucospilota was determined. Oxidation of the glucocerebroside with ozone afforded C13-fragment including the ante-iso moiety. The optically active C13-fragment was synthesized asymmetrically by using the Wittig reaction from chiral synton for comparison with the natural fragment.

chemical and pharmaceutical bulletin/chemical and pharmaceutical bulletin

Constituents of Holothuroidea, 16. Determination of Absolute Configuration of the Branched Methyl Group in Ante-iso Type Side Chain Moiety on Long Chain Base of Glucocerebroside from the Sea Cucumber Holothuria leucospilota