Design and Synthesis of New Classes of Heterocycle C-Glycoconjugates, and Carbon-Linked Sugar and Heterocycle Amino Acids by Asymmetric Multicomponent Reactions (AMCRs)

While chemical efficiency relies on several factors, the multi-component 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 β-amino acids via Mannich- and Reformatsky-type reactions, (c) C-glycosyl β-lactams via Staudinger reaction, and (d) heterocyclic α-amino acids (glycine and alanine) via the Biginelli and Hantzsch reactions. © 2006 American Chemical Society.