Synthesis of trans-Fused Octahydroisoindole-1-carboxylic Acids

文献类型： 外文期刊

第一作者： Laborda, Pedro

作者： Laborda, Pedro;Sayago, Francisco J.;Cativiela, Carlos;Laborda, Pedro;Gotor, Vicente

作者机构：

关键词： Amino acids; proline analogues; strecker; trans-fused ring systems; diastereoselectivity; lactamization

期刊名称：LETTERS IN ORGANIC CHEMISTRY （ 影响因子：0.867； 五年影响因子：0.865 ）

ISSN： 1570-1786

年卷期： 2018 年 15 卷 5 期

页码：

收录情况： SCI

摘要： trans-Fused octahydroisoindole-1-carboxylic acids are bicyclic proline analogues of potential interest in the search for new drugs. Within this work, the trans-fused octahydroisoindole system has been constructed using methyl trans-2-(hydroxymethyl) cyclohexane-1-carboxylate as the key synthetic precursor, in turn readily prepared from inexpensive cis-cyclohexane-1,2-dicarboxylic anhydride. Both the (1S*, 3aR*, 7aR*)- and the (1R*, 3aR*, 7aR*)-octahydroisoindole-1-carboxylic acids were prepared through the Strecker reaction of methyl trans-2-formylcyclohexane-1-carboxylate as the key step. Finally, (1S*, 3aR*, 7aR*)-octahydroisoindole-1-carboxylic acid was obtained with good yields in a highly stereoselective manner using (3aR*, 7aR*)-octahydroisoindole-1-one as a suitable scaffold.

分类号：

  • 相关文献
作者其他论文 更多>>

微信小程序