First synthesis and structural determination of blepharin and 1'-epiblepharin

Article abstract of DOI:10.1055/s-1991-28401

Total synthesis of the natural acetal-β-D-glucoside blepharin (1) and its C-2, epimer 9 by treatment of 2-bromo-2H-1,4-benzoxazin-3(4H)-one (5) with 2,3,4,6-tetra-O-acetyl-β-D-glucopyranose (6) is described. The relative and absolute configuration of 1 was determined by ¹H-NMR and X-ray analysis.