FACILE GENERATION AND TRAPPING OF ALPHA-OXO-O-QUINODIMETHANES - SYNTHESIS OF 3-ARYL-3,4-DIHYDROISOCOUMARINS AND PROTOBERBERINES

被引：34

作者：

KESSAR, SV

SINGH, P

VOHRA, R

KAUR, NP

VENUGOPAL, D

机构：

[1] Department of Chemistry, Panjab University

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1992年 / 57卷 / 25期

关键词：

D O I：

10.1021/jo00051a009

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Fluorodesilylation of o-((trimethylsilyl)methyl)benzoyl derivatives 5 in the presence of aromatic aldehydes and alkyl fumarates gives 3-aryl-3,4-dihydroisocoumarins 6 and alpha-tetralones 10, respectively. Reaction of 5 with 3,4-dihydroisoquinolinium salts 19 leads to 8-oxoberbines 21. Using this procedure, racemic hydrangenol, phyllodulcin, tetrahydropalmatine (22a), and canadine (22b) have been synthesized.

引用

页码：6716 / 6720

页数：5

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