Kamikawa K, Tachibana A, Sugimoto S, Uemura M
Department of Chemistry, Faculty of Integrated Arts and Sciences, Osaka Prefecture University, Sakai, Osaka 599-8531, Japan.
Org Lett. 2001 Jun 28;3(13):2033-6. doi: 10.1021/ol010076f.
[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.
[反应：见正文] 利用平面手性三羰基（芳基卤化物）铬配合物立体选择性地合成了万古霉素的轴向联芳基环系统。平面手性（芳基溴化物）铬配合物的两种对映体，即（+）-9和对映体（-）-9，可通过非对映选择性铃木-宫浦交叉偶联反应作为关键步骤，立体选择性地转移至万古霉素A-B环系统的绝对相同的关键中间体23。
