Michael S. Kellogg

Stereoselective synthesis of 6β-substituted penicillanates

Abstract Reduction of 6-substituted-6-halopenicillanates with tri-n-butyltin hydride can produce stereoselectively 6β-substituted derivatives.

Stereocontrol in aldol condensations. The role of solvent and cation in the condensation of acetaldehyde with the anion derived from benzyl 6,6-dibromopenicillanate.

Abstract Unique stereocontrol in aldolization at C6 of penicillanates through modification of solvent and cation has been observed.

Synthesis of novel sulfenamide-containing β-Lactams

Abstract Novel sulfenamide-containing [3,2,0]bicyclic β-lactams, which are potent inhibitors of human leukocyte elastase, were prepared.

Inhibition of human leukocyte elastase (HLE) by novel bicyclic β-lactams

Abstract Novel 3,2,0 bicyclic β-lactam sulfenamides and selected carbon isosteres are inhibitors of human leukocyte elastase. The comparative biological activity and hydrolytic stability of these compounds are described.