EnglishRacemic 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.
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http://hdl.handle.net/11568/6560| 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 |
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