HIGHLY VERSATILE STEREOSELECTIVE SYNTHESIS OF ALL EIGHT STEREOISOMERS OF BRANCHED-CHAIN TRIOLS STARTING FROM ASYMMETRIZED BIS(HYDROXYMETHYL)ACETALDEHYDES (BHYMA-ASTERISK)

摘要

All possible stereoisomers of triols of general formula 5 (R(1) allyl, R(2) = Me or allyl) have been synthesized stereoselectively starting from asymmetrized bis(hydroxymethyl)acetaldehyde (BHY-MA*), a novel chiral building block prepared through a chemoenzymatic methodology. This goal was realized through a sequence of protecting group-controlled nucleophilic additions and/or reductions performed on two side arms of this versatile building block.