1,6-Anhydro-β-D-glucopyranose in organic synthesis: preparation of a fragment for the synthesis of rosaramycin

Article abstract of DOI:10.1016/0008-6215(90)84072-3

1,6-Anhydro-β-D-glucopyranose has been used as the starting material for a synthesis of ethyl (E)-4-C-allyl-2,3,4,6-tetradeoxy-5,7-O-isopropylidene-8-O-methanesulphonyl-2,6-di-C-methyl-D-gulooct-2-enonate, which represents a synthetic unit equivalent to C-2/9 of the macrolide antibiotic rosaramycin.The synthesis involved a minimum of chromatography, and the extremely high level of regiochemical and stereochemical control was achieved by the use of epoxides at crucial C-C-bond-forming steps.A method was also developed, using tosylmethyl isocyanide, which converted a carbohydrate 6-aldehyde (19) directly into the corresponding homologated methyl ether.