Synthesis of 2-hydroxy-3-methylbut-3-enyl substituted coumarins and xanthones as natural products.: Application of the Schenck ene reaction of singlet oxygen with ortho-prenylphenol precursors

被引：35

作者：

Helesbeux, JJ ^{[1
]}

Duval, O ^{[1
]}

Dartiguelongue, C ^{[1
]}

Séraphin, D ^{[1
]}

Oger, JM ^{[1
]}

Richomme, P ^{[1
]}

机构：

[1] UFR Sci Pharmaceut & Ingn Sante, SONAS, F-49100 Angers, France

来源：

TETRAHEDRON | 2004年 / 60卷 / 10期

关键词：

Schenck ene reaction; photooxygenation; regioselectivity; ortho-(2-hydroxy-3-methylbut-3-enyl)phenols; coumarin; xanthone;

D O I：

10.1016/j.tet.2004.01.033

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Application of our original photooxidation-reduction methodology to prenylated dihydroxycoumarin and trihydroxyxanthone compounds led to the corresponding ortho-(2-hydroxy-3-methylbut-3-enyl)phenol derivatives with yields ranging from 8 to 65%. In most of the reported experiments, the oxidation products distribution, after the photooxygenation step, was controlled by the competition between the large group effect and the stabilising phenolic assistance effect. We also showed that ortho-(3-hydroxy-3-methylbut-1-enyl)phenol derivatives could be considered as biogenetic precursors of 2,2-dimethylbenzopyranic structures. (C) 2004 Elsevier Ltd. All rights reserved.

引用

页码：2293 / 2300

页数：8

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