PHOTOCYCLOADDITION OF ALPHA,BETA-UNSATURATED-GAMMA-LACTAM WITH ETHYLENE - SYNTHESIS OF CONFORMATIONALLY RESTRICTED GLUTAMATE ANALOGS, L-2-(2-CARBOXYCYCLOBUTYL)GLYCINES

Authors
TSUJISHIMA H NAKATANI K SHIMAMOTO K SHIGERI Y YUMOTO N OHFUNE Y
Citation
H. Tsujishima et al., PHOTOCYCLOADDITION OF ALPHA,BETA-UNSATURATED-GAMMA-LACTAM WITH ETHYLENE - SYNTHESIS OF CONFORMATIONALLY RESTRICTED GLUTAMATE ANALOGS, L-2-(2-CARBOXYCYCLOBUTYL)GLYCINES, Tetrahedron letters, 39(10), 1998, pp. 1193-1196
Citations number
12
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
39
Issue
10
Year of publication
1998
Pages
1193 - 1196
Database
ISI
SICI code
0040-4039(1998)39:10<1193:POAWE>2.0.ZU;2-8
Abstract
Both (2S,1'S,2'S)- and (2S,1'S,2'R)-isomers of 2-(2-carboxycyclobutyl) glycine (CBG-I, 1b) and (CBG-III, 2b) are synthesized in a stereoselec tive manner via a [2+2] photocycloaddition of alpha,beta-unsaturated-g amma-lactam 3 with ethylene in acetone. The extended type of isomer 1b showed a weak activity on group II metabotropic glutamate receptors ( mGluR2) of rat brain. (C) 1998 Elsevier Science Ltd. All rights reserv ed.