NITRONE CYCLOADDITION - AN APPROACH TO THE CYCLOPHANE ALKALOID (+/-)-LYTHRANIDINE

被引:18
作者
CARRUTHERS, W
COGGINS, P
WESTON, JB
机构
[1] UNIV EXETER,DEPT CHEM,STOCKER RD,EXETER EX4 4RJ,DEVON,ENGLAND
[2] WELLCOME RES LABS,BERKHAMSTED HP4 2DY,HERTS,ENGLAND
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1991年 / 03期
关键词
D O I
10.1039/p19910000611
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The synthesis of (+/-)-lythranidine 1, a cyclophane alkaloid from Lythrum anceps Makino, involves three interesting problems. These are the construction of the 17-membered ring, the formation of the trans-2,6-dialkylpiperidine and the establishment of the correct relative stereochemistry at the four asymmetric centres (C-3, C-5, C-9, C-11). In our approach to the synthesis of this alkaloid, the trans-dialkylpiperidine was formed via a nitrone cycloaddition reaction. Cyclisation to give the 17-membered ring was achieved using tris(triphenylphosphine)nickel(0), prepared in situ from bis(triphenylphosphine)nickel dichloride, and the di-iodide 9. Deprotection of macrocyclic biaryl 10 gave the (C-3, C-11) epimer of (+/-)-lythranidine.
引用
收藏
页码:611 / 616
页数:6
相关论文
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