Highly Versatile Stereoselective Synthesis of All Eight Stereoisomers of Branched-Chain Triols Starting from Asymmetrized Bis(hydroxymethyl)acetaldehydes (BHYMA)

Article abstract of DOI:10.1021/jo00129a029

All possible stereoisomers of triols of general formula 5 (R1=allyl, R2=Me or allyl) have been synthesized stereoselectively starting from asymmetrized bis(hydroxymethyl)acetaldehyde (BHYMA), 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.