SYNTHESIS OF HYDROXYQUINONES AND RELATED-COMPOUNDS - SEMISQUARIC ACIDS, (+/-)-TERREIC ACID, (+/-)-PEREZONE, AND (+/-)-ISOPEREZONE

被引：57

作者：

ENHSEN, A ^{[1
]}

KARABELAS, K ^{[1
]}

HEERDING, JM ^{[1
]}

MOORE, HW ^{[1
]}

机构：

[1] UNIV CALIF IRVINE,DEPT CHEM,IRVINE,CA 92717

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1990年 / 55卷 / 04期

关键词：

D O I：

10.1021/jo00291a015

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

tert-Butoxyquinones were prepared from the thermal ring expansion of 4-alkynyl-, 4-alkenyl-, and 4-aryl-£er£-butoxycyclobutenones and shown to be readily converted to hydroxyquinones upon treatment with trifluoroacetic acid at low temperature. This is a useful transformation since no reliable general route to hydroxyquinones has previously been available. The synthetic scope of this methodology as well as its specific utilization in the synthesis of a semisquaric acid, and the natural products, (±)-terreic acid, (±)-perezone, and (±)-isoperezone, are described. © 1990, American Chemical Society. All rights reserved.

引用

页码：1177 / 1185

页数：9

共 37 条

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