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- W1981902783 abstract "The ring-closing metathesis method is applied in the construction of conformationally restricted bicyclic nucleosides. From diacetone-D-glucose, the unsaturated bicyclic carbohydrate derivative 11 is efficiently obtained through two vinyl group Grignard additions, subsequent metathesis of the double bonds, and resolution of the stereochemistry by an oxidation/reduction reaction sequence. Two separate routes differing in the 3-O-protecting group are compared. Thus, an additional protecting step improves the yields significantly. Standard conversions of 11 give the bicyclic nucleoside 22 containing an olefinic moiety with a high potential for further functionalisation. As examples, two simple bicyclic ribo-nucleoside analogues 4 and 5, which are restricted to the unusual South-type conformations, are synthesised." @default.
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- W1981902783 date "2001-01-01" @default.
- W1981902783 modified "2023-10-09" @default.
- W1981902783 title "Synthesis of bicyclic nucleosides by ring-closing metathesis" @default.
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- W1981902783 doi "https://doi.org/10.1039/b101364p" @default.
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