A highly diastereoselective synthesis of dl-oleandrose

G Berti, G Catelani, F Colonna, L Monti

Index: Berti, G.; Catelani, G.; Colonna, F.; Monti, L. Tetrahedron, 1982 , vol. 38, # 20 p. 3067 - 3072

Full Text: HTML

Citation Number: 24

Abstract

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 ...