Enantioselective synthesis of Boc-protected norfuranomycins

Garner’s aldehyde is a suitable precursor for the synthesis of both isomers of Boc-protected epi-norfuranomycin. We demonstrate the utility of trisyl chloride as an effective leaving group in the dihydrofuran formation step. We also show that TEMPO/BAIB is an effective oxidant for α-amino alcohols avoiding epimerization of the labile α-proton of the product aldehyde.