Racemic oleandrose (2, 6-dideoxy-3-O-methyl-arabino-hexone) has been obtained starting from the Diels-Alder adduct between 4-methoxy-3-buten-2-one and isobutyl vinyl ether, which was converted into a mixture of the isobutyl β-and α-oleandrosides through hydroboration-oxidation. The latter reaction is highly diastereoselective since attack by borane takes place exclusively anti to the OMe group: none of the diasteroisomeric ...
