Abstract
A concise synthesis of C‐furanosides has been achieved, starting from unprotected d‐xylose and d‐arabinose. Both sugars reacted with hydroxylamine 6 to give the respective nitrones. These underwent in‐situ intramolecular 1,3‐dipolar cycloaddition reactions to give, in each case, a pair of diastereomeric derivatives of 7‐oxa‐1‐aza‐bicyclo[2.2.1]heptane 7 and 8. The ratio of chromatographically separable diastereoisomers could be changed by carrying out the reaction in the presence of weak Lewis acid. Both d‐xylose‐derived stereoisomers 7a and 8a were converted into d‐erythro‐C‐furanosides by tosylation or mesylation followed by catalytic hydrogenolysis. On the other hand, the formation of d‐threo‐C‐furanosides from d‐arabinose derivatives 7b and 8b under similar conditions was accompanied by the formation of minor amounts of polyhydroxyquinolizidines as a result of competitive N‐alkylation. The polyhydroxyquinolizidine side‐products were useful for the assignment of the configuration of the new compounds.
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