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Title

Synthesis of trans-fused octahydroisoindole-1-carboxylic acids

AuthorsLaborda, Pedro ; Sayago, Francisco J. ; Cativiela, Carlos ; Gotor, Vicente
KeywordsAmino acids
Proline analogues
Strecker
Trans-fused ring systems
Diastereoselectivity
Lactamization
Issue Date2018
PublisherBentham Science Publishers
CitationLetters in Organic Chemistry 15(5): 404-411 (2018)
Abstracttrans-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.
Publisher version (URL)https://doi.org/10.2174/1570178614666171130161203
URIhttp://hdl.handle.net/10261/187082
DOI10.2174/1570178614666171130161203
ISSN1570-1786
E-ISSN1875-6255
Appears in Collections:(ISQCH) Artículos
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