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Título: | Synthesis of trans-fused octahydroisoindole-1-carboxylic acids |
Autor: | Laborda, Pedro CSIC ORCID; Sayago, Francisco J. CSIC ORCID; Cativiela, Carlos CSIC ORCID; Gotor, Vicente | Palabras clave: | Amino acids Proline analogues Strecker Trans-fused ring systems Diastereoselectivity Lactamization |
Fecha de publicación: | 2018 | Editor: | Bentham Science Publishers | Citación: | Letters in Organic Chemistry 15(5): 404-411 (2018) | Resumen: | 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. | Versión del editor: | https://doi.org/10.2174/1570178614666171130161203 | URI: | http://hdl.handle.net/10261/187082 | DOI: | 10.2174/1570178614666171130161203 | ISSN: | 1570-1786 | E-ISSN: | 1875-6255 |
Aparece en las colecciones: | (ISQCH) Artículos |
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