SYNTHESIS OF NOVEL RACEMIC CARBOCYCLIC NUCLEOSIDE ANALOGUES DERIVED FROM 4,8-DIOXATRICYCLO[4.2.1.0^sup 3,7^]NONANE-9-METHANOL AND 4-OXATRICYCLO[4.3.1.0^sup 3,7^]DECANE-10-METHANOL, COMPOUNDS WITH ACTIVITY AGAINST COXSACKIE VIRUSES

摘要

(1R*,2R*,3R*,4S*)-7-Oxabicyclo[2.2.1]hept-5-ene-2,3-dimethanol (10) and (1R*,2R*,3R*,4S*)-bicyclo[2.2.2] oct-5-ene-2,3-dimethanol (14), which were prepared by the Diels-Alder reaction and subsequent reduction with lithium aluminium hydride, were treated with benzyl azidoformate to give benzyl N-[(1R*,2R*,3S*,6S*,7S*,9S*)-9-(hydroxymethyl)-4,8-dioxatricyclo[4.2.1.0^sup 3,7^] nonan-2-yl]carbamate (11) and benzyl N-[1R*,2R*,3R*,6R*,7S*,10S*)-10-(hydroxymethyl)-4-oxatricyclo[4.3.1.0^sup 3,7^] decan-2-yl]carbamate (15). Hydrogenolysis of carbamates 11 or 15 afforded (1R*,2R*,3S*,6S*,7S*,9S*)-2-amino-4,8-dioxatricyclo[4.2.1.0^sup 3,7^]-nonane-9-methanol (12) or (1R*,2R*,3R*,6R*,7S*,10S*)-2-amino-4-oxatricyclo[4.3.1.0^sup 3,7^]-decane-10-methanol (16). The amines 12 and 16 were transformed to thymine and purine nucleoside analogues. The target compounds were tested for the activity against Coxsackie virus. [PUBLICATION ABSTRACT]