Formation and cleavage of bisnoradamantane derivatives through SmI2 reductions

被引：13

作者：

Camps, P ^{[1
]}

Lukach, AE ^{[1
]}

Vázquez, S ^{[1
]}

机构：

[1] Univ Barcelona, Fac Farm, Quim Farmaceut Lab, E-08028 Barcelona, Spain

来源：

TETRAHEDRON | 2001年 / 57卷 / 12期

关键词：

cleavage reactions; coupling reactions; samarium diiodide; polycyclic aliphatic compounds;

D O I：

10.1016/S0040-4020(01)00096-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

引用

页码：2419 / 2425

页数：7

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