Synthesis of novel 6,11-O-bridged bicyclic ketolides via a palladium-catalyzed bis-allylation.
A bridging chemistry process was developed to form an ether bridge between 6-O and 11-O of erythromycin A via a tandem or stepwise palladium-catalyzed bis-pi-allylation. By applying this bridging process, new 6,11-O-bridged bicyclic ketolides (BBKs) were synthesized. These BBKs showed good antibacterial activities against the macrolide-susceptible strains as well as mef-resistant strains and served as a good core for further modifications to study the structure-activity relationship (SAR) and to overcome bacterial resistance. [reaction: see text]
Wang
Guoqiang
G
Enanta Pharmaceuticals, Inc., 500 Arsenal Street, Watertown, MA 02472, USA. wang@enanta.com
Niu
Deqiang
D
Qiu
Yao-Ling
YL
Phan
Ly Tam
LT
Chen
Zhigang
Z
Polemeropoulos
Alexander
A
Or
Yat Sun
YS