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2005
Nucleic acids
U 0700
Preparation of 2',3'-Oxirane-Fused Carbocyclic Nucleosides Based on N-Substi2-Azabicyclo[2.2.1]hept-5-en-3-ones. — Epoxidation of N-substituted azabi25- 200 tuted
cycloheptenones (I) with DMDO or MCPBA proceeds in an exo selective manner.
However, a stereodirecting influence of the OH-group in the derivative (III) results in
formation of the endo-product (IV). The attempted transformation of oxirane (IIb) into
oxirane-fused nucleosides via carbinol (V) is unsuccessful. Thus, an alternative route
to the targets (IX) is developed involving epoxidation of the unsaturated nucleoside
(VI). — (ISHIKURA*, M.; MATSUMOTO, K.; MURAKAMI, A.; Heterocycles 64
(2004) 241-248; Fac. Pharm. Sci., Health Sci. Univ. Hokkaido, Hokkaido 061, Japan;
Eng.) — Mais
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