Diels-Alder reactions with an α,β-unsaturated aldehydo-sugar. A route to 6-oxabicyclo[3.2.1]octanes

Article abstract of DOI:10.1016/S0040-4039(00)60786-4

Thermal and catalytic Diels-Alder reactions of 1 with 2,3-dimethyl-1,3-butadiene gave 4-formyl-5-glycocyclobexenes 2 and 3. Absolute configurations at the new chiral centers in the adducts are based on polarimetric correlation with known compounds. On reduction and acid treatment, the adducts 2 and 3 were converted into 6-oxabicyclo[3.2.1]octanes 13 and 15.