Synthetic transformations of higher terpenoids: XIV. Synthesis of pyrrololabdanoids from lambertianic acid

被引：0
|
作者：
S. V. Chernov
E. E. Shul’ts
M. M. Shakirov
G. A. Tolstikov
机构：
[1] Russian Academy of Sciences,Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Division
来源：
Russian Journal of Organic Chemistry | 2006年 / 42卷
关键词：
Methanol; Ester; Methyl Ester; Hydrazine; Pyrrole;
D O I：
暂无
中图分类号：
学科分类号：
摘要：
Treatment of lambertianic acid methyl ester with lead tetraacetate gave terpenoid 2,5-diacetoxydihydrofuran which reacted with primary amines to yield 3-terpenyl-substituted pyrrol-2(5H)-ones; the reaction with hydrazine led to the corresponding pyridazine derivative. The obtained furanoterpenoids underwent oxidative methoxylation by the action of N-chlorobenzenesulfonamide or N-bromosuccinimide in methanol. 2,5-Dimethoxydihydrofurans thus formed were smoothly converted into 3-substituted furan-2(5H)-one in acid medium. Hydrogenation of 2,5-dimethoxydihydrofurans, followed by treatment with amines, gave 1,3-disubstituted pyrroles.
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页码：828 / 838
页数：10
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