文献类型： 外文期刊
作者： Laborda, Pedro 1 ; Sayago, Francisco J. 1 ; Cativiela, Carlos 1 ; Gotor, Vicente 3 ;
作者机构： 1.Univ Zaragoza CSIC, Inst Sintesis Quim & Catalisis Homogenea, Dept Quim Organ, Zaragoza 50009, Spain
2.Jiangsu Acad Agr Sci, Inst Plant Protect, Nanjing 210014, Jiangsu, Peoples R China
3.Univ Oviedo, Dept Quim Organ & Inorgan, E-33071 Oviedo, Asturias, Spain
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.
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