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含氮四烯的双环关环复分解反应：双环生物碱骨架的高效构建及其在羽扇豆碱四种立体异构体及其衍生物合成中的应用

Double ring-closing metathesis reaction of nitrogen-containing tetraenes: efficient construction of bicyclic alkaloid skeletons and synthetic application to four stereoisomers of lupinine and their derivatives.

作者信息

Ma Shengming, Ni Bukuo

机构信息

State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, P. R. China.

出版信息

Chemistry. 2004 Jul 5;10(13):3286-300. doi: 10.1002/chem.200305581.

DOI:10.1002/chem.200305581
PMID:15224338
Abstract

The double ring-closing metathesis reaction of nitrogen-containing tetraenes was studied. The selectivity of the fused/dumbbell-type products can be controlled by the electronic/steric effects of the substituents attached to the C[double bond]C bonds and the s-cis/s-trans conformational ratios of the substrates. This methodology has also been successfully applied to the enantioselective synthesis of four stereoisomers of lupinine and their derivatives.

摘要

研究了含氮四烯的双环闭环复分解反应。稠合型/哑铃型产物的选择性可通过连接在C=C键上的取代基的电子/空间效应以及底物的s-顺式/s-反式构象比来控制。该方法也已成功应用于羽扇豆碱及其衍生物的四种立体异构体的对映选择性合成。

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