Synthetic Transformations of Methylenelactones of Eudesmanic Type. Behavior of Isoalantolactone under the Conitions of Heck Reaction

被引：20

作者：

Belovodskii, A. V. ^{[1
]}

Shults, E. E. ^{[1
]}

Shakirov, M. M. ^{[1
]}

Bagryanskaya, I. Yu. ^{[1
]}

Gatilov, Yu. V. ^{[1
]}

Tolstikov, G. A. ^{[1
]}

机构：

[1] Russian Acad Sci, Vorozhtsov Novosibirsk Inst Organ Chem, Siberian Div, Novosibirsk 630090, Russia

来源：

RUSSIAN JOURNAL OF ORGANIC CHEMISTRY | 2010年 / 46卷 / 11期

基金：

俄罗斯基础研究基金会;

关键词：

SESQUITERPENOIDS; LACTONES;

D O I：

10.1134/S1070428010110199

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

By Heck reaction of isoalantolactone with aryl bromides or aryl iodides (3aR,4aS,8aR,9aR,E)-3-arylmethylidene-8a-methyl-5-methylidenedecahydronaphtho[2,3-b]furan-2(3H)-ones and (4aS,8aR,9aS)-3-arylmethyl-8a-methyl-5-methylidene-4a,5,6,7,8,8a,9,9a-octahydronaphtho[2,3-b]furan-2(4H)-ones, products of the double bond shift, were synthesized. The yields of the arylation products depend on the nature of the catalytic system and on the structure of the aryl halide. The structures of(3aR,4aS,8aR,9aR,E)-3-(3,4-dimethoxybenzylidene)-8a-methyl-5-methylidenedecahydronaphtho[2,3-b] furan-2(3H)-one and (4aS,8aR,9aS)-3-(2-methylsulfanylbenzyl)-8a-methyl-5-methylidene-4a,5,6,7,8,8a,9,9a-octahydronaphtho[2,3-b]furan-2(4H)-one were proved by XRD analysis.

引用

页码：1719 / 1734

页数：16

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