Synthesis of carbapenem skeleton / 国际药学研究杂志

ABSTRACT

Objective To investigete a new synthetic route for carbapenem skeleton(1)for industrial production. Methods (3S,4R)-4-acetoxy-3-[(1R)-(tert-butyldimethylsilyloxy)ethyl]azetidin-2-one(4-AA)was used as raw material,and 1 was obtained from it through a homemade chiral auxiliary zinc powder catalyzed Reformatsky reaction,hydrolysis,the introduction of β-carboxyl es?ter structure,deprotection,cyclization,and activation by diphenyl chlorophosphate. The each key process was optimized,and the structures of intermediate and target compounds were confirmed by MS,GC-MS and 1H NMR.Results and Conclusion The total yield was 19.9%.The improved process conditions are mild,easy to operate,and suitable for industrial production.