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Synthesis 1990; 1990(10): 945-950
DOI: 10.1055/s-1990-27062
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Synthesis of Indole 2′,3′-Dideoxyribonucleosides

Frank Seela* , Werner Bourgeois
  • *Laboratorium für Organische und Bioorganische Chemic, Fachbereich Biologie/Chemie, Universität Osnabrück, Barbarastr.7, D-4500 Osnabrück, Federal Republic of Germany
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Publication Date:
17 September 2002 (online)

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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.