Catalytic asymmetric synthesis of CPZEN-45

A catalytic asymmetric total synthesis of CPZEN-45 (1), anti-XDR-TB agent, was accomplished using a direct aldol reaction of a glycine Schiff base (3) and uridine-derived aldehyde (4) catalyzed by Zn(II)-(R,R)-linked-BINOL complex to give the desired stereoisomer selectively. The diazepinone ring system, another key structural element, was successfully constructed by vinyl halide-amide coupling promoted by Cu(I) salt. (C) 2016 Elsevier Ltd. All rights reserved.