Formation and cleavage of bisnoradamantane derivatives through SmI2 reductions
Formation and cleavage of bisnoradamantane derivatives through SmI2 reductions
复制标题
DOI：
10.1016/s0040-4020(01)00096-5
复制
发表时间：
2001-03-17
期刊：
影响因子：
2.1
通讯作者：
Vázquez, S
中科院分区：
文献类型：
--
作者：
Camps, P;Lukach, AE;Vázquez, S
双降金刚烷骨架的应变通过以下方式显示：（i）在硅胶柱色谱法下，三环[3.3.0.0（3.7）]辛烷-1，5-二醇，2a容易同酮化为外-7-羟基-顺式-双环[3.3.0]辛烷-3-酮，3a，和（ii）在尝试的SmI 2-分子内频哪醇化下，1，5-二甲基-3，7-二新戊酰基三环[3.3.0.0（3.7）]辛烷，9的C3-C7键断裂，得到双环[3.3.0]辛烷二酮。相反，2a通过顺式-双环[3.3.0]辛烷-3，7-二酮1a的SmI 2-频哪醇化得到。(C)2001爱思唯尔科技有限公司版权所有。
The strain of the bisnoradamantane skeleton is shown by: (i) the easy homoketonization of tricyclo[3.3.0.0(3.7)]octane-1,5-diol, 2a, to exo-7-hydroxy-cis-bicyclo[3.3.0]octan-3-one, 3a, under silica gel column chromatography, and (ii) the cleavage of the C3-C7 bond of 1,5-dimethyl-3,7-dipivaloyltricyclo[3.3.0.0(3.7)]octane, 9, to give bicyclo[3.3.0]octane diketones, under attempted SmI2-intramolecular pinacolization. In contrast, 2a was obtained by SmI2-pinacolization of cis-bicyclo[3.3.0]octane-3,7-dione, 1a. (C) 2001 Elsevier Science Ltd. All rights reserved.