cis- and trans-3-(3-indolyl)proline derivatives as conformationally restricted analogues of tryptophan

Authors
Damour, D Pulicani, JP Vuilhorgne, M Mignani, S
Citation
D. Damour et al., cis- and trans-3-(3-indolyl)proline derivatives as conformationally restricted analogues of tryptophan, SYNLETT, (6), 1999, pp. 786-788
Citations number
35
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
SYNLETT
ISSN journal
09365214 → ACNP
Issue
6
Year of publication
1999
Pages
786 - 788
Database
ISI
SICI code
0936-5214(199906):6<786:CATDAC>2.0.ZU;2-8
Abstract
A method for the diastereoselective generation of 3-indolyl-3-proline deriv atives has been developed. The [3+2] cycloaddition reaction of 3-vinylindol es with dimethyl N-ethoxycarbonyl-N-methoxymethylaminomalonate in the prese nce of TiCl4, afforded the title compounds after acid hydrolysis and decarb oxylation reactions. These new amino acids may be viewed as conformationall y restricted mimetics of tryptophan.