Chiral synthesis of polyketide-derived natural products. Part 3. Stereocontrolled synthesis of a chiral fragment corresponding to both the C-1—C-4 and C-9—C-12 units of erythromycin A fromD-glucose

Abstract

A chiral synthon, 3,6-dideoxy-1,2-O-isopropylidene-3-C-methyl-β-L-lyxo-hexofuranos-5-ulose (7), for the total synthesis of erythromycin A (1) corresponding to both the C-1—C-4 and C-9—C-12 fragments was synthesiszed highly stereoselectively from D-glucose (2)via stereoselective hydrogenation of 3,6-dideoxy-1,2-O-isopropylidene-3-C-methyl-α-D-glycero-hex-3-enofuranos-5-ulose (12).