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Using an asymmetric Diels-Alder reaction of (S)S-3- (2-pyridylsulfinyl) acrylate with furan, a highly enantioselective synthesis of a common key intermediate (+) - (1) was achieved, and this was successfully converted to C-nucleosides, D-showdomycin (2) and D-3, 4-O-isopropylidene-2, 5-anhydroallose (3).

chemical and pharmaceutical bulletin/chemical and pharmaceutical bulletin

Successful asymmetric Diels-Alder approach to optically active C-nucleosides. Enantioselective total synthesis of D-showdomycin and D-2,5-anhydroallose derivatives.