A practical synthesis of antiviral cyclopropane nucleoside A-5021

Authors
Onishi, T Matsuzawa, T Nishi, S Tsuji, T
Citation
T. Onishi et al., A practical synthesis of antiviral cyclopropane nucleoside A-5021, TETRAHEDR L, 40(50), 1999, pp. 8845-8847
Citations number
7
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
40
Issue
50
Year of publication
1999
Pages
8845 - 8847
Database
ISI
SICI code
0040-4039(199912)40:50<8845:APSOAC>2.0.ZU;2-V
Abstract
(1'S,2'R)-9-[[1',2'-bis(hydroxymethyl)cycloprop-1'-yl]methyl]guanine (A-502 1, 1) was synthesized from optically active cyclopropane lactone 2 by emplo ying: (1) selective reduction of the ester; (2) alkylation of 2-amino-6-chl oropurine; and (3) reductive opening of the lactone ring. This route elimin ates the protection steps to give 1 in a good yield and is of practical val ue. (C) 1999 Elsevier Science Ltd. All rights reserved.