Synthetic study of ciguatoxin. Absolute configuration of the C2 hydroxy group

Article abstract of DOI:10.1016/S0040-4020(97)00071-9

The absolute stereochemistry of the secondary alcohol of the 1,2-dihydroxybutenyl substituent of ciguatoxin (1) was shown to be S by comparing (he split CD curve of ciguatoxin tetra-p-bromobenzoate (2) with those of di- and tri-p-bromobenzoates of AB ring fragments that were synthesized enaotioselectively.