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.

A HIGHLY DIASTEREOSELECTIVE SYNTHESIS OF DL-OLEANDROSE

CATELANI, GIORGIO;
1982

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 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.
Catelani, Giorgio; Catelani, G; Colonna, F; Monti, L.
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11568/6560
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