Design and synthesis of new classes of heterocyclic C-glycoconjugates and carbon-linked sugar and heterocyclic amino acids by asymmetric multicomponent reactions (AMCRs).
While chemical efficiency relies on several factors, the multicomponent reaction (MCR) approach was considered as a powerful synthetic tool for preparing target molecules of biological relevance in an efficient manner. Four classes of new bioactive molecules were designed and synthesized by asymmetric MCRs, in some cases with the cooperation of polymer-assisted solution-phase (PASP) technique. These include (a) C-glycosyl dihydropyrimidines and dihydropyridines via Biginelli and Hantzsch cyclocondensations, (b) C-glycosyl beta-amino acids via Mannich- and Reformatsky-type reactions, (c) C-glycosyl beta-lactams via Staudinger reaction, and (d) heterocyclic alpha-amino acids (glycine and alanine) via the Biginelli and Hantzsch reactions.
Dondoni
Alessandro
A
Dipartimento di Chimica, Laboratorio di Chimica Organica, Università di Ferrara, Via L. Borsari 46, I-44100 Ferrara, Italy. adn@dns.unife.it
Massi
Alessandro
A
D000596:Amino Acids / Q000737:chemistry*; D002241:Carbohydrates / Q000737:chemistry*; D002244:Carbon / Q000737:chemistry*; D006001:Glycoconjugates / Q000138:chemical synthesis / Q000737:chemistry*; D006031:Glycosylation; D006571:Heterocyclic Compounds / Q000138:chemical synthesis / Q000737:chemistry*
D000596:Amino Acids; D002241:Carbohydrates; D006001:Glycoconjugates; D006571:Heterocyclic Compounds; D002244:Carbon