THE STEREOSELECTIVE SYNTHESIS OF (E)-ALKENE DIPEPTIDE ISOSTERES

Authors
YONG YF LIPTON MA
Citation
Yf. Yong et Ma. Lipton, THE STEREOSELECTIVE SYNTHESIS OF (E)-ALKENE DIPEPTIDE ISOSTERES, Bioorganic & medicinal chemistry letters, 3(12), 1993, pp. 2879-2882
Citations number
39
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Medicinal
Journal title
Bioorganic & medicinal chemistry letters → ACNP
ISSN journal
0960894X
Volume
3
Issue
12
Year of publication
1993
Pages
2879 - 2882
Database
ISI
SICI code
0960-894X(1993)3:12<2879:TSSO(D>2.0.ZU;2-Y
Abstract
A diastereo- and enantio- selective synthesis of the (E)-alkene dipept ide isostere of L-Ala-L-Ala from L-alanine has been developed which pr oceeds via stereocontrolled addition of a (Z)-vinyllithium reagent fol lowed by a [2,3]-Wittig rearrangement. The synthesis proceeds in seven steps overall from L-alanine methyl ester. It is believed that this a pproach will provide a fairly general and convenient route to isostere s of a number of different dipeptides.