Abstract
AbstractSynthesis of north‐5'‐methylbicyclo[3.1.0]hexyl purine and pyrimidine nucleosides with an ethynyl group at C‐3' position has been successfully accomplished by a facile method. Methylbicyclo[3.1.0]hexanone (±)‐5 having three contiguous chiral centers was remarkably simply constructed only by four steps containing a carbenoid insertion reaction in the presence of rhodium(II) acetate dimer and CuSO4, giving a correct relative stereochemistry of the generated three chiral centers. Upon Grignard reaction of (±)‐5 with ethynylmagnesium bromide, exclusive diastereoselectivity was observed. Condensation of glycosyl donor (±)‐9 with purine nucleobase afforded only the desired N9‐alkylated nucleoside, while condensation with pyrimidine, N3‐benzoylated uracil gave the desired N1‐alkylated nucleoside (±)‐13 with the undesired O2‐alkylated nucleoside (±)‐14. Probably, (±)‐14 would be formed due to steric hindrance caused upon approaching for N1‐alkylation.
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