A facile synthesis of fused aromatic spiroacetals based on the 3,4,3′,4′-tetrahydro-2,2′-spirobis(2H-1-benzopyran) skeleton

被引：34

作者：

Brimble, Margaret A. ^{[1
]}

Flowers, Christopher L. ^{[1
]}

Trzoss, Michael ^{[1
]}

Tsang, Kit Y. ^{[1
]}

机构：

[1] Univ Auckland, Dept Chem, Auckland 1, New Zealand

来源：

TETRAHEDRON | 2006年 / 62卷 / 25期

关键词：

D O I：

10.1016/j.tet.2006.04.026

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The facile synthesis of a series of aromatic 6,6-spiroacetals based on the parent 3,4,3',4'-tetrahydro-2,2'-spirobis(2H-1-benzopyran) heterocyclic system is reported. Key steps included the use of a Sonogashira coupling for the synthesis of an aryl acetylene that was coupled to an aryl aldehyde to form a propargyl alcohol intermediate. Hydrogenation of the alkynol followed by oxidation produced a masked dihydroxy ketone that upon treatment with trimethylsilyl bromide underwent deprotection and cyclisation to the fused aromatic spiroacetal. (c) 2006 Elsevier Ltd. All rights reserved.

引用

页码：5883 / 5896

页数：14

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