Synthesis of trans-fused Octahydroisoindole-1-carboxylic Acids

Title:Synthesis of trans-fused Octahydroisoindole-1-carboxylic Acids

Volume: 15 Issue: 5

Author(s): Pedro Laborda, Francisco J. Sayago , Carlos Cativiela*Vicente Gotor*

Affiliation:

• Departamento de Quimica Organica, Instituto de Sintesis Quimica y Catalisis Homogenea, Universidad de Zaragoza- CSIC, 50009 Zaragoza,Spain

• Departamento de Quimica Organica e Inorganica, Universidad de Oviedo, 33071 Oviedo (Asturias),Spain

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

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.

Cite this article as:

Laborda Pedro , Sayago J. Francisco , Cativiela Carlos *, Gotor Vicente *, Synthesis of trans-fused Octahydroisoindole-1-carboxylic Acids, Letters in Organic Chemistry 2018; 15 (5) . https://dx.doi.org/10.2174/1570178614666171130161203