Asymmetric synthesis of novel quaternary alpha-hydroxy-delta-lactam dipeptide surrogates.
Application of the Sharpless AD protocol to a series of alpha-(E)-benzylidene-delta-lactam precursors followed by selective deoxygenation provided efficient synthetic routes to the chiral quaternary alpha-hydroxy-gammalactam derivatives 4 and 5. These functionalized intermediates and the diol precursors 3 are regarded as novel types of D-Phe-Pro dipeptide surrogates that are useful as enzyme active site probes.
Minami
N K
NK
Department of Medicinal Chemistry, Corvas International, Inc., San Diego, CA 92121, USA.
Reiner
J E
JE
Semple
J E
JE
D004151:Dipeptides / Q000138:chemical synthesis* / Q000737:chemistry; D007769:Lactams / Q000737:chemistry*; D020836:Protein Structure, Quaternary
D004151:Dipeptides; D007769:Lactams