Two epimeric chiral cyclopentylglycines (-)-16 and (+)-17, functionalised with a carboxy group cis to the amino acid group, were prepd. starting from chiral 2-amino-3-oxo-norbornanecarboxylic acid deriv. I by combining two classical reactions such as the Diels-Alder and retro-Claisen reactions. Compds. II (R1= CO2H, R2= NH2; and R1= CO2H, R2= NH2) are non-proteinogenic amino acids of biol. interest contg. conformational constraints in which the skeletons of both 2-aminoadipic acid and 2-aminopimelic acid are included
Enantioselective synthesis of epimeric cis-3-carboxycyclopentylglycines / F. Caputo, F. Clerici, M.L. Gelmi, S. Pellegrino, T. Pilati. - In: TETRAHEDRON-ASYMMETRY. - ISSN 0957-4166. - 17:1(2006), pp. 61-67. [10.1016/j.tetasy.2005.11.011]
Enantioselective synthesis of epimeric cis-3-carboxycyclopentylglycines
F. ClericiSecondo
;M.L. Gelmi;S. PellegrinoPenultimo
;
2006
Abstract
Two epimeric chiral cyclopentylglycines (-)-16 and (+)-17, functionalised with a carboxy group cis to the amino acid group, were prepd. starting from chiral 2-amino-3-oxo-norbornanecarboxylic acid deriv. I by combining two classical reactions such as the Diels-Alder and retro-Claisen reactions. Compds. II (R1= CO2H, R2= NH2; and R1= CO2H, R2= NH2) are non-proteinogenic amino acids of biol. interest contg. conformational constraints in which the skeletons of both 2-aminoadipic acid and 2-aminopimelic acid are included
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