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Asymmetric synthesis of novel quaternary alpha-hydroxy-delta-lactam dipeptide surrogates
N K Minami1, J E Reiner, J E Semple
1Department of Medicinal Chemistry, Corvas International, Inc., San Diego, CA 92121, USA.
Bioorganic & Medicinal Chemistry Letters
|September 25, 1999
Abstract:
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.