A facile synthesis of aryl spirodioxines based on a 3H,3′H-2,2′-Spiro-bi(benzo[b][1,4]dioxine) skeleton

被引:15
|
作者
Brimble, Margaret A. [1 ]
Liu, Yen-Cheng [1 ]
Trzoss, Michael [1 ]
机构
[1] Univ Auckland, Dept Chem, Auckland 1142, New Zealand
来源
SYNTHESIS-STUTTGART | 2007年 / 9卷 / 09期
关键词
D O I
10.1055/s-2007-966016
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The synthesis of a series of 6,6-bisbenzannulated spiroketals containing a 3H,3'H-2,2'-spirobi(benzo[b][1,4]dioxine) ring system is reported. The key step involves addition of a monobenzyl-protected catechol to the epoxide unit of a glycidol bearing a benzyl-protected catechol. The resultant alcohol adduct is oxidized to a ketone that then undergoes hydrogenation and acid-catalyzed cyclization to produce the desired spirodioxines.
引用
收藏
页码:1392 / 1402
页数:11
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