Artículos de revistas
From Amino Acids to Nature-Inspired Molecular Scaffolds: Incorporation of Medium-Sized Bridged Heterocycles into a Peptide Backbone
Fecha
2014-10Registro en:
la Venia, Agustina; Ventosa Andres, Pilar; Hradilova, Ludmila; Krchnak, Viktor; From Amino Acids to Nature-Inspired Molecular Scaffolds: Incorporation of Medium-Sized Bridged Heterocycles into a Peptide Backbone; American Chemical Society; Journal of Organic Chemistry; 79; 21; 10-2014; 10378-10389
0022-3263
CONICET Digital
CONICET
Autor
la Venia, Agustina
Ventosa Andres, Pilar
Hradilova, Ludmila
Krchnak, Viktor
Resumen
Novel molecular scaffolds comprising two to four bridged and fused heterocycles were synthesized from amino acids using seven-membered endocyclic N-acyliminium ions as key intermediates in acid-mediated tandem reactions with internal nucleophiles. This complexity-generating synthesis proceeds with high efficiency and with full stereocontrol of the newly generated stereogenic center. These results have extended the scope of medium-sized cyclic iminium ion chemistry, making it applicable as a regio- and stereoselective synthetic strategy for the generation of complex polycyclic structures. Furthermore, its compatibility with the traditional Merrifield synthesis of peptides on solid supports allowed the incorporation of the previously unexplored conformationally restricted cyclic systems into peptides without a need to independently synthesize the scaffold