A concise route to the C2-symmetric tricyclic skeleton of ryanodine
A concise route to the C2-symmetric tricyclic skeleton of ryanodine
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DOI：
10.1016/j.tetlet.2008.12.054
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发表时间：
2009-03-04
影响因子：
1.8
通讯作者：
Inoue, Masayuki
中科院分区：
文献类型：
--
作者：
Hagiwara, Koji;Himuro, Masafumi;Inoue, Masayuki
兰诺定是一种有效的钙通道调节剂。在这封信中，我们报道了高度取代的兰诺定三环体系的10步合成。通过2，5-二甲苯-1，4-二醇的脱芳构化和SML(2)催化的八元1，5-二酮的还原偶联反应，有效地引入了三环[3.3.2.0(2，6)]正十二烷体系中连续的四个全取代碳。(C)2008爱思唯尔有限公司。保留所有权利。
Ryanodine is a potent calcium channel modulator. In this Letter, we report the 10-step synthesis of the highly substituted tricyclic ring system of ryanodine. Diels-Alder reaction via dearomatization of 2, 5-dimethylbenzene-1,4-diol and subsequent Sml(2)-mediated reductive coupling of eight-membered 1,5-diketone efficiently introduced the four consecutive fully substituted carbons of the tricyclo[3.3.2.0(2,6)]decane system. (C) 2008 Elsevier Ltd. All rights reserved.