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KMID : 0617320010100010167
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Journal of Pharmacetical Sceiences Ewha Womans University
2001 Volume.10 No. 1 p.167 ~ p.171
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Synthesis and Antiviral Activity of Fluoro-substituted Apio Dideoxynucleosides
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Hong, Joon Hee
Kim, Hea Ok/Moon, Hyung Ryong/Jeong, Lak Shin
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Abstract
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Novel fluoro-substituted apio dideoxynucleosides ((±)-3a and (±)03b) were efficiently synthesized starting from 1,3-dihydroxyacetone via Homer-Emmons olefination as a key step. Cyclization of fluoro ester(±)-6 under acidic conditions to the fluorolactone was smoothly proceeded in favor of trans-fluorolactone due to the favorable transition state with equatorial hydroxymethyl substituent. Unfortunately, the final nucleosides(±)-3a and (±)3b were found to be inactive against several viruses such as HIV-1, HSV-1,HSV-2 and HCMV.
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