Anodic C16-C21 fragmentation of catharanthine in methanol. Synthesis of 16-methoxycleavamine

被引:6
作者
Tabakovic, I [1 ]
Gunic, E [1 ]
Gasic, MJ [1 ]
机构
[1] UNIV BELGRADE, FAC SCI, YU-11000 BELGRADE, YUGOSLAVIA
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2 | 1996年 / 12期
关键词
D O I
10.1039/p29960002741
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Two-electron controlled potential oxidation of catharanthine (Cath) affords 2 in 65% yield, Compound 2 is reduced to 16-methoxycleavamine in 95% yield, Cyclic voltammetry experiments show that catharanthine hydrochloride (CathH(+)) in methanol solution in the presence of 2,6-lutidine exists in acid-base equilibrium with Cath as a free base which is oxidized at 0.7 V vs, SCE, Oxidation of Cath to Cath(+) and fragmentation of the C16-C21 bond is assumed to occur via a concerted mechanism.
引用
收藏
页码:2741 / 2745
页数:5
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