A 2ND-GENERATION SYNTHESIS OF SCALEMIC 3,5,5-TRISUBSTITUTED PYRROLIN-4-ONES - INCORPORATION OF FUNCTIONALIZED AMINO-ACID SIDE-CHAINS

Authors
SMITH AB BENOWITZ AB FAVOR DA SPRENGELER PA HIRSCHMANN R
Citation
Ab. Smith et al., A 2ND-GENERATION SYNTHESIS OF SCALEMIC 3,5,5-TRISUBSTITUTED PYRROLIN-4-ONES - INCORPORATION OF FUNCTIONALIZED AMINO-ACID SIDE-CHAINS, Tetrahedron letters, 38(22), 1997, pp. 3809-3812
Citations number
22
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
38
Issue
22
Year of publication
1997
Pages
3809 - 3812
Database
ISI
SICI code
0040-4039(1997)38:22<3809:A2SOS3>2.0.ZU;2-Q
Abstract
To access mimics of peptidal beta-strands (1), scalemic 3,5,5-trisubst ituted pyrrolin-4-ones bearing the tyrosine, serine, and lysine side-c hains have been generated via cyclization of metalated imino esters an d deprotection. The functionalized imino esters were prepared by asymm etric alkylation of a common oxazolidinone precursor (2) derived from L-prenylglycine. (C) 1997 Elsevier Science Ltd.