A general route to 4-C-branched sugars. Synthesis of methyl α-caryophylloside Original Research Article

The total synthesis of methyl 3,6-dideoxy-4-C-(d-altro-1,3,4,5 tetrahydroxyhexyl)-α-d-xylo-hexopyranoside, the methyl glycoside of the recently isolated 4-C-branched sugar caryophyllose, has been completed in a stereoselective and convergent manner. The synthesis of this dodecose relies on the diiodosamarium mediated coupling of two six-carbon fragments: a cyclic ketone and an acid chloride.