SYNTHESES OF (2S,3S)-[4,4,4-H-2(3)]- AND (2S,3R)-[4,4,4-H-2(3)] PENICILLAMINE

(2S,3S)-[4,4,4-H-2(3)]- and (2S,3R)-[4,4,4-H-2(3)]Penicillamine -ami-n o-3-mercapto-3-methyl-[4,4,4-H-2(3)]butanoic acids) were synthesized f rom benzyl (1S,3S,6R)-6-(phenoxyacetylamino)penicillanate 1-oxide and allyl (1R,3S,6R)-6-phthalimidopenicillanate 1-oxide, respectively. The two key steps are the stereospecific sulfur oxidation of the 6-phenox yacetylamino- versus the 6-phthalimidopenicillanic acid to provide the (1S) and (1R) sulfoxides, respectively, and the exclusive exchange of the hydrogen atoms of the C-2 methyl that are cis to oxygen of the su lfoxide group with the deuterium of deuterium oxide.