RESEARCHES ON ANTIVIRAL AGENTS .31. SYNTHESIS AND TRANSFORMATIONS OF RACEMIC AND CHIRAL 6-OXIRANYL PYRIMIDINONES

Authors
BOTTA M SALADINO R LAMBA D NICOLETTI R
Citation
M. Botta et al., RESEARCHES ON ANTIVIRAL AGENTS .31. SYNTHESIS AND TRANSFORMATIONS OF RACEMIC AND CHIRAL 6-OXIRANYL PYRIMIDINONES, Tetrahedron, 49(27), 1993, pp. 6053-6070
Citations number
30
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
49
Issue
27
Year of publication
1993
Pages
6053 - 6070
Database
ISI
SICI code
0040-4020(1993)49:27<6053:ROAA.S>2.0.ZU;2-Q
Abstract
The synthesis of epoxides 3, 4 and 6 has been described. The transform ation of 3 into C-6 alkylated uracils 22a-e, 23a-d, 24 and 25 is also reported The chiral epoxide (S)-(+)-3 has been prepared via a modified Solladie procedure, while the ZnCl2- DIBAH reduction step failed to g ive the expected enantiomer (R)-(-)-3. This result has been discussed on the ground of molecular modeling studies.