CONFORMATIONALLY CONSTRAINED AMINO-ACIDS .2. ON THE SYNTHESIS OF 4-SUBSTITUTED 8-MEMBERED CYCLIC TRYPTOPHAN DERIVATIVES

Authors
CHUNG JYL WASICAK JT NADZAN AM
Citation
Jyl. Chung et al., CONFORMATIONALLY CONSTRAINED AMINO-ACIDS .2. ON THE SYNTHESIS OF 4-SUBSTITUTED 8-MEMBERED CYCLIC TRYPTOPHAN DERIVATIVES, Synthetic communications, 22(7), 1992, pp. 1039-1048
Citations number
15
Journal title
Synthetic communications → ACNP
ISSN journal
00397911
Volume
22
Issue
7
Year of publication
1992
Pages
1039 - 1048
Database
ISI
SICI code
0039-7911(1992)22:7<1039:CCA.OT>2.0.ZU;2-9
Abstract
The thermal lactamization of 4-(carboethoxy)-methyl-tryptophan ethyl e ster (5), prepared from 4-(carboethoxy)methyl-indole 3 via Gilchrist's method, in refluxing xylene followed by saponification provided the 8 -membered cyclic tryptophan derivative 1. Selective reduction of lacta m 6 via the iminium ion 9 furnished the cyclic tryptophan derivative 2 .