Citation
N. Gauvry et F. Huet, Novel preparation of cis,cis-trisubstituted cyclopropane nucleosides, TETRAHEDRON, 55(5), 1999, pp. 1321-1328
Citations number
29
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020
→ ACNP
Volume
55
Issue
5
Year of publication
1999
Pages
1321 - 1328
Database
ISI
SICI code
0040-4020(19990129)55:5<1321:NPOCCN>2.0.ZU;2-R
Abstract
Novel cyclopropane nucleosides, cis-2',cis-3'-bis(hydroxymethyl)cyclopropyl
thymine 4a and adenine 4b were synthesized. The stereoselective rin:: cont
raction of cyclobutyl bromohydrin 8 afforded cyclopropyl aldehyde 9 with a
cis,cis configuration. After oxidation, conversion to amide and Hofmann's r
earrangement, methyl carbamate 12 was obtained. Its basic hydrolysis yielde
d amine 13, then the target molecules were obtained by construction of base
s. (C) 1999 Elsevier Science Ltd. All rights reserved.