A CONVENIENT, HIGH-YIELD SYNTHESIS OF L-OLEANDROSE AND L-OLEANDRAL

Article abstract of DOI:10.1016/0008-6215(89)84090-X

A short, practical synthesis of L-oleandrose (2,6-dideoxy-3-O-methyl-L-arabino-hexose) from L-arabinose has been achieved.The synthesis is satisfactory for large-scale preparation of oleandrosylating intermediates, and employs dithiolane formation for protection of the aldehyde group during deoxygenation and methylation steps, and Wittig chain-extension to 2-deoxyhexose derivatives.Useful intermediates in the introduction of oleandrose glycosides into natural products, such as the 1,4-dibenzoates and the methyl glycosides, were prepared and characterized.L-Oleandral (1,5-anhydro-2,6-dideoxy-3-O-methyl-L-arabino-hex-1-enitol), another useful intermediate for glycosylation, was prepared from 3,4-di-O-acetyl-L-rhamnal by deacetylation, and regioselective methylation with stannous chloride-diazomethane.