A PHOTOCHEMICAL ROUTE TO THE PROTOBERBERINE SKELETON

被引：11

作者：

COYLE, JD ^{[1
]}

BRYANT, LRB ^{[1
]}

CRAGG, JE ^{[1
]}

CHALLINER, JF ^{[1
]}

HAWS, EJ ^{[1
]}

机构：

[1] POLYTECH WOLVERHAMPTON, DEPT PHYS SCI, WOLVERHAMPTON WV1 1LY, ENGLAND

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1985年 / 06期

关键词：

D O I：

10.1039/p19850001177

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Irradiation of Mannich bases obtained from phthalimides, formaldehyde, and 1,2,3,4-tetrahydroisoquinolines, and carrying methoxy or methylenedioxy substituents gave, in moderate yield, pentacyclic photoproducts. These underwent acid-promoted reaction leading to 13-hydroxydibenzo-[a,g]quinolizin-8-ones, one of which was 13-hydroxy-8-oxoxylopinine. Reduction to remove the 8,13-oxygenated functions was not achieved. Unsymmetrical substrates derived from 3,4-dimethoxyphthalimide gave a mixture of regio- and stereo-isomers in the photocyclization, with no strong preference for one orientation of reaction.

引用

页码：1177 / 1180

页数：4

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