Protoberberines from Reissert compounds VII.: Diastereoselective reduction of 1-benzylated isoquinoline Reissert compounds and synthesis of oxoberbine carbonic acids

被引：9

作者：

Reimann, E ^{[1
]}

Grasberger, F ^{[1
]}

Polborn, K ^{[1
]}

机构：

[1] Univ Munich, Inst Pharm, D-81377 Munich, Germany

来源：

MONATSHEFTE FUR CHEMIE | 2000年 / 131卷 / 01期

关键词：

Reissert compounds; diastereoselective reduction; oxazoloisoquinolinones; X-ray crystal structure; 13a-carboxy-8-oxoberbines; 8-oxoberbines;

D O I：

10.1007/s007060050008

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Reduction of 1-substituted Reissert compounds 1 by NaBH3CN in a mixture of trifluoroacetic and acetic acid diastereoselectively affords oxazoloquinolinones 2 as the main products; in addition, aldehydes 3 and 4 and the dibenzyl derivative 5 are formed. The structure of 2 was characterized by X-ray crystallography. Upon treatment with potassium hydroxide in ethanol, 2 is cleaved and reacylated yielding the 13a-carboxyberbinones 7. Decarboxylation of 7 occurs readily to afford a 1:2 mixture of berbinones 10 and 11.

引用

页码：73 / 84

页数：12

共 16 条

[1] NOVEL CYCLOADDITIONS OF ISOQUINOLINE REISSERT SALTS [J].