Efficient route to optically pure polyfunctionalized cyclooctanes
Efficient route to optically pure polyfunctionalized cyclooctanes
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DOI：
10.1016/s0040-4039(01)02126-8
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发表时间：
2002-01-07
影响因子：
1.8
通讯作者：
Le Merrer, Y
中科院分区：
文献类型：
--
作者：
Gravier-Pelletier, C;Andriuzzi, O;Le Merrer, Y
以D-甘露糖醇为原料，用1，2：5，6-双环氧化合物合成了对映体纯的高度官能化的八元碳环。关键的环化步骤涉及使用Grubbs催化剂的1，9-二烯的复分解或由先前二烯的氧化裂解产生的1，8-二醛的频哪醇偶联。在闭环复分解环化的特定情况下，构象限制的二烯相比，灵活的一个的影响进行了评估。(C)2002爱思唯尔科技有限公司版权所有。
A short and efficient synthesis of enantiopure highly functionalized eight-membered carbocyclic rings is described from 1,2:5,6-bis-epoxides issued from D-mannitol. The key cyclization step involves the metathesis of 1,9-diene using Grubbs' catalyst or the pinacolic coupling of 1,8-dialdehyde resulting from the oxidative cleavage of the previous diene. In the specific case of ring-closing metathesis cyclization, the influence of a conformationally restricted diene compared to that of a flexible one has been evaluated. (C) 2002 Elsevier Science Ltd. All rights reserved.