Synthesis of Indole 2′,3′-Dideoxyribonucleosides
- 1 January 1990
- journal article
- research article
- Published by Georg Thieme Verlag KG in Synthesis
- Vol. 1990 (10) , 945-950
- https://doi.org/10.1055/s-1990-27062
Abstract
The syntheses of 1,3,7-trideaza-2′,3′-dideoxyadenosine (1) and its 2′,3′-didehydroderivative (2b) as potential anti-HIV compounds are described. Nucleobase anion glycosylation of 4-nitroindole (4) with 1-chloro-2-deoxy-3,5-bis-O-(4-methylbenzoyl)-α-D-erythro- pentofuranose (5) yields 1-[2-deoxy-3,5-bis-O-(4-methylbenzoyl)- β-D-erythro-pentofuranosyl]-4-nitro-1H-indole (6a) stereoselectively in 85% yield. Upon detoluoylation the 3′-hydroxyl group was removed by two different routes using a mesylation/elimination process.Keywords
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