STUDIES ON THE SYNTHESIS OF THE APLYSIATOXINS: SYNTHESIS OF A SELECTIVELY-PROTECTED FORM OF THE C27-C30 (DIHYDROXYBUTANOATE) MOIETY OF OSCILLATOXIN A

Article abstract of DOI:10.1016/S0040-4039(01)83850-8

A protected form of (R)-3,4-dihydroxybutanoic acid bearing a benzyl protecting group at the C₄ hydroxyl and a dimethylthexylsilyl protecting group at the C₃ hydroxyl was synthesized via a selective Ag(I)-mediated monobenzylation of (R)-methyl 3,4-dihydroxybutanoate.An alternative synthetic route from a chiral allylic ether was successful but problematic.The acid could be clenly coupled to a model for the C₃-C₁₁ moiety of the aplysiatoxins.