SYNTHESIS OF URACIL POLYOXIN-C FROM URIDINE

Authors
EVINA CM GUILLERM G
Citation
Cm. Evina et G. Guillerm, SYNTHESIS OF URACIL POLYOXIN-C FROM URIDINE, Tetrahedron letters, 37(2), 1996, pp. 163-166
Citations number
21
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
37
Issue
2
Year of publication
1996
Pages
163 - 166
Database
ISI
SICI code
0040-4039(1996)37:2<163:SOUPFU>2.0.ZU;2-X
Abstract
An improved procedure is reported for the asymmetric synthesis of urac il polyoxin C (UPOC) from 2',3'-O-isopropylideneuridine-5'-aldehyde. T he methodology described here is based on the highly diastereocontroll ed formation of 1-(beta-D-allofuranosyl)uracil and its facile conversi on into the corresponding 2,5'-O-cyclouridine derivative, a key step f or the stereocontrolled formation of the terminal alpha-amino acid of UPOC.