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Synthesis of trans-fused Octahydroisoindole-1-carboxylic Acids

[ Vol. 15 , Issue. 5 ]

Author(s):

Pedro Laborda, Francisco J. Sayago , Carlos Cativiela* and Vicente Gotor*   Pages 404 - 411 ( 8 )

Abstract:


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.

Keywords:

Amino acids, proline analogues, strecker, trans-fused ring systems, diastereoselectivity, lactamization.

Affiliation:

Departamento de Quimica Organica, Instituto de Sintesis Quimica y Catalisis Homogenea, Universidad de Zaragoza- CSIC, 50009 Zaragoza, Departamento de Quimica Organica, Instituto de Sintesis Quimica y Catalisis Homogenea, Universidad de Zaragoza- CSIC, 50009 Zaragoza, Departamento de Quimica Organica, Instituto de Sintesis Quimica y Catalisis Homogenea, Universidad de Zaragoza- CSIC, 50009 Zaragoza, Departamento de Quimica Organica e Inorganica, Universidad de Oviedo, 33071 Oviedo (Asturias)

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