α-Amino acids with electrically charged and polar uncharged side chains as chiral synthon: Application to the synthesis of bioactive alkaloids (1996-Dec, 2013)

Abstract

Enantiomerically pure α-amino acids (α-AAs) are, for a long time, considered as a major class of chiral pools. Their employment in the enantioselective synthesis of natural products has made enormous impact in the general organic synthesis. This review is an effort to discuss the state of the art of synthetic methodologies in which the α-amino acids with electrically charged and polar uncharged side chains (i.e. Arginine, Histidine, Lysine, Aspartic acid, Glutamic acid, Serine, Threonine, Asparagine, Glutamine, Cysteine) have been transformed into final bioactive alkaloids and related diversity during the period 1996 to December 2013. In general, two principles are followed to harness the potential of the amino acids: one in which the original chiral center is preserved and the other in which the chiral center is resorted to create new stereocenters by stereoinduction. This article is arranged with individual amino acid in the alphabetical order as a source of starting material towards description of alkaloids. Key synthetic steps are mentioned in each description of an alkaloid for the benefit of future organic practitioners.