Journal
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
Volume 18, Issue 1, Pages 220-222Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.bmcl.2007.10.095
Keywords
carbocyclic nucleoside; Grubbs reaction; fluorinated cyclopentyl derivative; Mitsunobu coupling.
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Funding
- NATIONAL INSTITUTE OF ALLERGY AND INFECTIOUS DISEASES [U19AI056540] Funding Source: NIH RePORTER
- NIAID NIH HHS [AI 56540, U19 AI056540-05] Funding Source: Medline
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5'-Fluoro-5'-deoxyaristeromycin (2) has been prepared via a Mitsunobu coupling of (1S,2S,3R,4S)-2,3-(cyclopentylidenedioxy)-4-fluoromethylcyclopentan-1-ol with N-6-bis-boc protected adenine. This procedure is adaptable to preparing a number of 5'-fluoro-5'-deoxycarbocyclic nucleoside analogs with diversity in the heterocyclic base. Antiviral analysis found promising activity for 2 toward measles but no other viruses. No cytotoxicity was observed for 2. (C) 2007 Elsevier Ltd. All rights reserved.
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