Asymmetric synthesis of novel quaternary alpha-hydroxy-delta-lactam dipeptide surrogates

Authors
Minami, NK Reiner, JE Semple, JE
Citation
Nk. Minami et al., Asymmetric synthesis of novel quaternary alpha-hydroxy-delta-lactam dipeptide surrogates, BIOORG MED, 9(17), 1999, pp. 2625-2628
Citations number
30
Categorie Soggetti
Chemistry & Analysis
Journal title
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
ISSN journal
0960894X → ACNP
Volume
9
Issue
17
Year of publication
1999
Pages
2625 - 2628
Database
ISI
SICI code
0960-894X(19990906)9:17<2625:ASONQA>2.0.ZU;2-L
Abstract
Application of the Sharpless AD protocol to a series of alpha-(E)-benzylide ne-delta-lactam precursors followed by selective deoxygenation provided eff icient synthetic routes to the chiral quaternary alpha-hydroxy-gamma-lactam derivatives 4 and 5. These functionalized intermediates and the diol precu rsors 3 are regarded as novel types of D-Phe-Pro dipeptide surrogates that are useful as enzyme active site probes. (C) 1999 Elsevier Science Ltd. All rights reserved.