Stereoselective synthesis of the axially chiral A-B ring system of vancomycin utilizing a planar chiral arene chromium complex.
[reaction: see text] The axial biaryl ring system of vancomycin was stereoselectively synthesized by utilizing a planar chiral tricarbonyl(arylhalide)chromium complex. Both enantiomers of the planar chiral (arylbromide)chromium complexes, (+)-9 and ent-(-)-9, can be stereoselectively transferred to an absolutely identical key intermediate 23 for the vancomycin A-B ring system by the diastereoselective Suzuki-Miyaura cross-coupling reaction as key step.
Kamikawa
K
K
Department of Chemistry, Faculty of Integrated Arts and Sciences, Osaka Prefecture University, Sakai, Osaka 599-8531, Japan.
Tachibana
A
A
Sugimoto
S
S
Uemura
M
M
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry; D017608:Chromium Compounds / Q000737:chemistry; D008968:Molecular Conformation; D014640:Vancomycin / Q000138:chemical synthesis* / Q000737:chemistry
D000900:Anti-Bacterial Agents; D017608:Chromium Compounds; D014640:Vancomycin