In an effort to design dipeptide structural mimics of protein and peptide reverse-turns, a series of 5,5-, 6,5-, and 7,5-fused 2-oxo-1-azabicycloalkane amino acids has been synthesized. A new and convenient synthetic route utilizing a Horner−Emmons reaction followed by double-bond reduction has been used to prepare the bicyclic lactams in high yields.
Synthesis of azabicycloalkane amino acid scaffolds as reverse-turn inducer dipeptide mimics / M. Angiolini, A. Araneo, L. Belvisi, E. Cesarotti, A. Checchia, L. Crippa, L. Manzoni, C. Scolastico. - In: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. - ISSN 1434-193X. - 2000:14(2000), pp. 2571-2581. [10.1002/1099-0690(200007)2000:14<2571::AID-EJOC2571>3.0.CO;2-D]
Synthesis of azabicycloalkane amino acid scaffolds as reverse-turn inducer dipeptide mimics
A. Araneo;L. Belvisi;E. Cesarotti;
2000
Abstract
In an effort to design dipeptide structural mimics of protein and peptide reverse-turns, a series of 5,5-, 6,5-, and 7,5-fused 2-oxo-1-azabicycloalkane amino acids has been synthesized. A new and convenient synthetic route utilizing a Horner−Emmons reaction followed by double-bond reduction has been used to prepare the bicyclic lactams in high yields.
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