aS,7S-absolute configuration of natural (-)-colchicine and allo-congeners.
The aS,7S-absolute configuration of (-)-colchicine (1) and (-)-N-acetylcolchinol methyl ether (3, NCME) suggested on the basis of 1H NMR data and negative Cotton effects at about 260 nm (EtOH) is firmly established by an X-ray analysis of urea 5, a compound derived from 3. Binding of these compounds to tubulin requires an aS-configuration of the biaryl system.
Brossi
A
A
Natural Products Section, NIDDK, National Institutes of Health, Bethesda, MD 20892.
Boyé
O
O
Muzaffar
A
A
Yeh
H J
HJ
Toome
V
V
Wegrzynski
B
B
George
C
C
D003078:Colchicine; D008968:Molecular Conformation
D003078:Colchicine