TOTAL SYNTHESIS OF DOCOSANOYLAMINO]-16-METHYLHEPTADECANE-1,3,4,-TRIOL3,4-DIBENZOATE, A PARTIALLY PROTECTED CERAMIDE PART OF SPONGE CEREBROSIDES

ydocosanoylamino]-16-methylheptadecane-1,3,4-triol 3.4-dibenzoate 32, a partially protected ceramide part of a cerebroside from the marine s ponge Halichondria japonica, has been synthesized from L-ascorbic acid , and its absolute stereochemistry has been determined. The key steps in the synthesis include the regioselective ring opening of chiral epo xide 5 with a 2-alkyl-2-lithio-1,3-dithiane and the introduction of a hydroxymethylene synthon using Dondoni's protocol to assemble C(1) and C(2) functionality.