A NOVEL OXIDATION STAGE IN THE CHEMISTRY OF PROTOBERBERINE ALKALOIDS - SYNTHESIS OF 7,8-DEHYDROBERBINES

被引：17

作者：

SUAU, R

SILVA, MV

VALPUESTA, M

机构：

[1] Departamento de Química Organica, Facultad de Ciencias Universidad de Málaga

来源：

TETRAHEDRON | 1991年 / 47卷 / 30期

关键词：

BERBINES; OXIDATION; IODINE; QUINOLIZIDINE CONFORMATION;

D O I：

10.1016/S0040-4020(01)86534-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

1,2-substituted berbines, such as (-)-caseamine, (-)-caseadine and (-)-O-methylcaseadine, are partially oxidized by iodine to the 7,8-dehydroberbines, while the 2,3-substituted berbines are oxidized all the way to the protoberberinium salts. This different behaviour is interpreted in terms of the preferred cis or trans B/C quinolizidine conformation of the starting berbines.

引用

页码：5841 / 5846

页数：6

共 13 条

[1]

[Anonymous], 1988, ALKALOIDS CHEM PHARM

[2]

Beecher C. W. W., 1988, ALKALOIDS CHEM BIOL, V6, P297

[3] ALKALOIDS OF STEPHANIA GLABRA . A DIRECT CHEMICAL CORRELATION OF ABSOLUTE CONFIGURATION OF SOME BENZYLTETRAHYDROISOQUINOLINE PROAPORPHINE AND APORPHINE ALKALOIDS . A NEW PROTOBERBERINE ALKALOID [J].