Target-directed synthesis of antibacterial drug candidate GSK966587.
An efficient enantioselective total synthesis of the potent antibiotic GSK966587 was accomplished. Highlights of the synthesis include two innovative Heck reactions, a highly selective zincate base directed ortho-metalation, Sharpless asymmetric epoxidation, and a fully convergent final step fragment coupling.
Voight
Eric A
EA
GlaxoSmithKline, Synthetic Chemistry Department, 709 Swedeland Road, P.O. Box 1539, King of Prussia, Pennsylvania 19406, USA. eric.a.Voight@abbott.com
Yin
Hao
H
Downing
Susan V
SV
Calad
Stacie A
SA
Matsuhashi
Hayao
H
Giordano
Ilaria
I
Hennessy
Alan J
AJ
Goodman
Richard M
RM
Wood
Jeffery L
JL
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D015394:Molecular Structure; D009287:Naphthyridines / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D013237:Stereoisomerism
D000900:Anti-Bacterial Agents; C553069:GSK966587; D009287:Naphthyridines