SIMPLE SYNTHESIS OF PRIMIN AND ITS ANALOGS VIA LITHIATION OF PROTECTED GUAIACOL

被引：12

作者：

BIEBER, LW ^{[1
]}

CHIAPPETA, AD ^{[1
]}

SOUZA, MADE ^{[1
]}

GENERINO, RM ^{[1
]}

NETO, PR ^{[1
]}

机构：

[1] UNIV FED PERNAMBUCO,CURSO MESTRADO CIENCIAS FARMACEUT,BR-50739 RECIFE,PE,BRAZIL

来源：

JOURNAL OF NATURAL PRODUCTS | 1990年 / 53卷 / 03期

关键词：

D O I：

10.1021/np50069a029

中图分类号：

Q94 [植物学];

学科分类号：

071001 ;

摘要：

A simple two-step synthesis of primin [Id] and related 6-substituted 2-methoxy-l,4-benzoquinones has been developed. Tetrahydropyranylated guaiacol [5] was treated with n-butyllithium followed by alkylation with alkyl, allyl, or benzyl bromides. Hydrolysis to the corresponding 6-substituted 2-methoxyphenols 2a-2g and subsequent oxidation catalyzed by salcomine afforded high yields of the quinones 1a-lg. © 1990, American Chemical Society. All rights reserved.

引用

页码：706 / 709

页数：4

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