Synthesis of 2-iodobenzamides and 3-(iodoacetamido)benzamides linked to D-galactose and their tri-n-butyltin hydride-mediated radical carbocyclization reactions

[摘要] Starting from methyl 6-O-allyl-4-azido-2,3-di-O-benzyl-4-deoxy-α-D-galactopyranoside, four new derivatives containing 2-iodobenzamido and 3-(iodoacetamido)benzamido groups were synthesized. These four compounds were submitted to tri-n-butyltin hydride mediated radical cyclization reactions, resulting in two macrolactams from 11- and 15-endo aryl radical cyclization. The corresponding four hydrogenolysis products were also obtained. The structures of the new compounds were elucidated by 1H and 13C NMR spectroscopy, DEPT, COSY, HMQC and HMBC experiments.

[学科分类] 化学（综合）

[关键词] aryl radical cyclization;macrolactam;D-galactose derivatives.