Synthesis of novel racemic carbocyclic nucleosides derived from 5,6-disubstituted norbornene
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MicHubMarMil
Éditeur:
Ins
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Novel class of the carbocyclic nucleosides based on bicyclo[2.2.1]heptene/heptane was prepared by two approaches. Thymine analogues were synthesized starting from methyl (1 R *,4 S *)-bicyclo[2.2.1]hepta-2,5-diene-2-carboxylate 1 by Michael addition of the thymine salt to the double bond as the key step. The yield and ratio of the isomers of this reaction depended on the used base (DBU, K 2 CO 3 ). Purine nucleoside analogues were synthesized by the linear synthesis, the purine nucleobase was build-up on the amino group. The amino groups ( exo / endo configuration) were introduced to the scaffold by the Curtius rearrangement. Norbornene analogues were converted to saturated and cis -hydroxylated nucleoside derivatives. [(1 R *,2 S *,3 S *,4 S *)-3-(6-Chloro-9 H -purin-9-yl)bicyclo[2.2.1]hept-5-en-2-yl]methanol ( 13a ) and [(1 R *,2 R *,3 R *,4 S *)-3-(6-chloro-9 H -purin-9-yl)bicyclo[2.2.1]hept-5-en-2-yl]methanol ( 13b ) showed moderate activity against Coxsackie virus CVB3.
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