David J. Claffey

Synthetic route to optically-pure metabolites of butadiene, and their chiral GC separation

Abstract The four possible stereoisomers of 3,4-epoxybutane-1,2-diol were stereospecifically synthesized in excellent yields, and fully characterized, as part of a study on the stereochemical aspects of butadiene metabolism and toxicity. GC methodology was developed whereby baseline separation of the enantiomeric pairs was achieved.

MULTIGRAM-SCALE STEREOSELECTIVE SYNTHESIS OF MESO-1,3-BUTADIENE BISEPOXIDE

ABSTRACT meso-1,3-Butadiene bisepoxide, a potential building block for natural product synthesis and of interest as a toxic metabolite of butadiene, was synthesized in multi-gram scale in two steps from meso-erythritol in good overall yield.

SOLID PHASE SYNTHESIS OF (R)- AND (S)-13C-BUTADIENE MONOXIDE

Abstract A stereospecific route to (R)- and (S)- [ 13 C]-butadiene monoxide was developed using (R)- or (S)-glycidaldehyde and a polymer-supported Wittig reagent.