Stereoselective synthesis of vinylogous peptides

Authors
Grison, C Geneve, S Halbin, E Coutrot, P
Citation
C. Grison et al., Stereoselective synthesis of vinylogous peptides, TETRAHEDRON, 57(23), 2001, pp. 4903-4923
Citations number
49
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
57
Issue
23
Year of publication
2001
Pages
4903 - 4923
Database
ISI
SICI code
0040-4020(20010604)57:23<4903:SSOVP>2.0.ZU;2-X
Abstract
A trans or cis ethenyl group has been inserted between the alpha -carbon an d the carboxyl group of alpha -aminoacids by Horner stereoselective olefina tion of a-aminoaldehydes. Numerous pure cia and trans vinylogous alpha -ami noacids have been obtained thus and coupled with aminopartners by classical methods. The versatility of the method was illustrated by the preparation of a [trans vinylogous-Gly(3)]Leu-enkephalin. (C) 2001 Elsevier Science Ltd . All rights reserved.