A NOVEL SYNTHESIS OF METHYLENECYCLOPROPANE SPIRO-LINKED WITH CYCLOALKANES VIA A CYCLIZATION OF ALLYLIC EPOXIDES AND ITS APPLICATION TO A SYNTHESIS OF FUSED 3-METHYLFURANS

被引：16

作者：

SATOH, T ^{[1
]}

KAWASE, Y ^{[1
]}

YAMAKAWA, K ^{[1
]}

机构：

[1] SCI UNIV TOKYO, FAC PHARMACEUT SCI, ICHIGAYA FUNAGAWARA MACHI, SHINJUKU KU, TOKYO 162, JAPAN

来源：

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN | 1991年 / 64卷 / 04期

关键词：

D O I：

10.1246/bcsj.64.1129

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Ring closure of allylic epoxides derived from l-chloroalkyl phenyl sulfoxides and cyclic ketones with lithium diisopropylamide (LDA) in 3-Exo-Tet mode gave spiro-linked methylenecyclopropanes having a hydroxyl group in good yields. Oxidation of these compounds gave ketones, which were then treated with p-toluenesulfonic acid in 1,4-dioxane or DMSO at 100-degrees-C to give fused 3-methylfurans in good overall yields. This procedure was applied to a synthesis of methofuran from 4-methylcyclohexanone.

引用

页码：1129 / 1135

页数：7

共 24 条

[1] FURANNULATION STRATEGY FOR SYNTHESIS OF THE NATURALLY-OCCURRING FUSED 3-METHYLFURANS - EFFICIENT SYNTHESIS OF EVODONE AND MENTHOFURAN AND REGIOSELECTIVE SYNTHESIS OF MATURONE VIA A LEWIS-ACID CATALYZED DIELS-ALDER REACTION - SOME COMMENTS FOR ITS MECHANISTIC ASPECTS
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[10] Green metal-free synthesis of spiro-fused 3,4-pyrazolo[4,3:5,6]pyrido[2,3-d]pyrimidine derivatives via deamination cyclization reactions in aqueous medium
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