Reductive deoxygenation of ortho-hydroxyaromatic aldehydes to 1,2-bis(hydroxyaryl)ethanes: application to the synthesis of ethylene bridged calixarene-analogous metacyclophanes
作者:Suchitra Bhatt、Sandip K. Nayak
DOI:10.1016/j.tetlet.2009.07.156
日期:2009.10
and convenient protocol for the synthesis of hexahydroxy[2.1.2.1.2.1]- and octahydroxy[2.1.2.1.2.1.2.1]metacyclophanes from 4-substituted phenol in four steps has been developed. The synthetic route involved the preparation of the key intermediate 1,2-bis(5-substituted-2-hydroxyphenyl)ethanes in good yields via (i) formylation of 4-substituted phenol, (ii) reductive deoxygenation of 5-substituted 2-hydroxy
已经开发了一种新颖且方便的方案,可在四个步骤中从4-取代的苯酚合成六羟基[2.1.2.1.2.1]-和八羟基[2.1.2.1.2.1.2.1]甲基环烷。合成途径涉及通过(i)4-取代的苯酚的甲酰化,(ii)5-取代的2-的还原性脱氧,以高收率制备关键的中间体1,2-双(5-取代的2-羟基苯基)乙烷。羟基芳族醛与低价钛试剂和(iii)催化加氢。通过用甲醛在回流的二甲苯中以甲醛对上述中间体进行碱催化的大环化来制备间环烷。