Synthesis of (S)-(-)-N-acetylcolchinol using intramolecular biaryl oxidative coupling.
An asymmetric synthesis of the tubulin polymerisation inhibitor (S)-(-)-N-acetylcolchinol is reported based on an intramolecular biaryl oxidative coupling of a 1,3-diarylpropyl acetamide intermediate using phenyliodonium bis(trifluoroacetate) as the final step. Three syntheses of the penultimate 1,3-diarylpropyl acetamide intermediate (S)-(-)-N-[1-[3-(tert-butyldimethylsilyloxy)phenyl)]-3-(3,4,5-trimethoxyphenyl)propyl] acetamide are described which differ in the means by which the stereogenic centre was introduced.
Besong
Gilbert
G
School of Chemistry, Leeds University, Leeds LS2 9JT, UK.
Jarowicki
Krzysztof
K
Kocienski
Philip J
PJ
Sliwinski
Eric
E
Boyle
F Thomas
FT
D000081:Acetamides / Q000737:chemistry; D003078:Colchicine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D018360:Crystallography, X-Ray; D015394:Molecular Structure; D009861:Onium Compounds / Q000737:chemistry; D010084:Oxidation-Reduction; D013237:Stereoisomerism; D050257:Tubulin Modulators / Q000138:chemical synthesis / Q000737:chemistry
D000081:Acetamides; D009861:Onium Compounds; D050257:Tubulin Modulators; C510883:phenyliodonium; C017815:N-acetylcolchinol; D003078:Colchicine