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 cymarosides are formed. The only side-products are small amounts of the isobutyl β- and α-amicetodies formed by a demthoxylation occuring during the hydroboration step.
|Autori interni:||CATELANI, GIORGIO|
|Autori:||BERTI G; CATELANI G; COLONNA F; MONTI L|
|Titolo:||A HIGHLY DIASTEREOSELECTIVE SYNTHESIS OF DL-OLEANDROSE|
|Anno del prodotto:||1982|
|Digital Object Identifier (DOI):||10.1016/0040-4020(82)80194-4|
|Appare nelle tipologie:||1.1 Articolo in rivista|