A HIGHLY DIASTEREOSELECTIVE SYNTHESIS OF DL-OLEANDROSE

Article abstract of DOI:10.1016/0040-4020(82)80194-4

Racemic oleandrose (2,6-dideoxy-3-O-methyl-arabino-hexose) 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 diastereoisomeric cymarosides are formed.The only side-products are small amounts of the isobutyl β- and α-amicetosides formed by a demethoxylation occuring during the hydroboration step.