Synthesis of (2S,4R,5R)-4,5,6-trihydroxynorleucine and 5-hydroxynorvaline from precursors obtained by an unusual rearrangement in a 5,6-dihydro-2-pyrone

Article abstract of DOI:10.1016/0040-4020(96)00767-3

2-Acetamido-4,6-O-benzylidene-2,3-dideoxy-D-erythro-hex-2-enono-1,5-la ctone (2), readily prepared from D-glucosamine, undergoes a rearrangement on treatment with tin(IV) chloride which leads to 3-acetamido-2-pyrone (3) and 2-acetamido-2,3-dideoxy-4,6-O-f