Abstract
A general synthetic route to the title compounds is outlined which involves: ( a) the Grignard reduction of methyl 2- O-benzoyl-4,6- O-benzylidene-α- d- ribo-hexopyranosid-3-ulose; ( b) the dehydration of the derived methyl 2- O-acetyl-3- C-alkyl-4,6- O-benzylidene-α- d-allopyranoside, with thionyl chloride-pyridine, at 0°, to provide the methyl 2- O-acetyl-3- C-alkyl-4,6- O-benzylidene-3-deoxy-α- d- erythro-hex-3-enopyranoside; and finally ( c) the acid-catalyzed fragmentation of the alkene to the title compounds. Synthetic routes from the title compounds to some novel branched-chain sugars and some rotenoids are proposed.
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