N-(2,3,4,5,6-PENTAFLUOROPHENYL)MALEIMIDE AS A POWERFUL DIENOPHILE IN DEAROMATIZING DIELS-ALDER REACTIONS

被引：3

作者：

Hagiwara, Koichi ^{[1
]}

Iwatsu, Masafumi ^{[1
]}

Urabe, Daisuke ^{[1
]}

Inoue, Masayuki ^{[1
]}

机构：

[1] Univ Tokyo, Grad Sch Pharmaceut Sci, Bunkyo Ku, Tokyo 1130033, Japan

来源：

HETEROCYCLES | 2015年 / 90卷 / 01期

关键词：

Diels-Alder Reaction; Dearomatization; Carbocycle; Quaternary Carbon; Total Synthesis; ACRYLATE-TYPE DIENOPHILES; INTERNAL ACTIVATION; MALEIC ANHYDRIDE; MOLECULAR FLASK; MALEIMIDES; DERIVATIVES; BENZENE;

D O I：

10.3987/COM-14-S(K)23

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Here we demonstrate that N-(2,3,4,5,6-pentafluorophenyl)maleimide effectively promotes dearomatizing Diels-Alder reactions of 2,5-dimethylbenzene-1,4-diol and naphthalen-2-ol derivatives. The present reactions successfully converted the sp(2)-rich components to the desired products with multiple sp(3)-carbons in a single step. The adduct was further derivatized into the intermediate for our synthesis of 9-demethy1-10,15-dideoxyryanodol, an analogue of a sp(3)-rich natural product, in two steps.

引用

页码：659 / 672

页数：14

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