Amino acid chirons: a tool for asymmetric synthesis of heterocycles

Abstract

As a result of their easy availability in enantiomerically enriched form and their possession of synthetically transformable diverse functional groups, amino acids have been extensively used by synthetic organic and medicinal chemists as a chiral pool for access to heterocycles (monocycles, bicycles or polycycles, either bridged or fused). This review describes the syntheses of diverse asymmetric heterocycles with various membered rings (n = 3-9) followed by benzo or heteroannulated ones, for the period from 1996 to Dec. 2013. It details solution phase synthetic methodologies in which the naturally occurring α-amino acid is incorporated, totally or partially, into the final product.

Recent Advances in Substrate-Controlled Asymmetric Induction Derived from Chiral Pool α-Amino Acids for Natural Product Synthesis

“…Suh et al synthesized polyhydroxylated indolizidine alkaloids, 1-deoxy-6,8a-di-epi-castanospermine (4) and 1-deoxy-6-epi-castanospermine (7), that can act as selective α-glycosidase inhibitors [8,9]. L-Proline was utilized as a platform to construct the indolizidine skeleton, as shown in Scheme 1.…”

“…Chirally pure α-amino acids are very useful materials due to diversity of functional group and ease of commercial use [7]. The α-amino acids described in this review are illustrated in Figure 2.…”

“…This strategy is one of the best methods available to synthetic organic chemists for establishing pivotal stereocenters in optically active compounds [3][4][5][6][7]. The chiral pool is a versatile tool, comprising naturally occurring chiral molecules such as carbohydrates, amino acids, terpenes, alkaloids, and hydroxyacids [2,6].…”

“…Chiral pool materials are also inexpensive and commercially available, making them adequate for use in accessing natural products and bioactive compounds [2]. The usage of the chiral pool in asymmetric synthesis can be classified in three general categories, as shown in Figure 1: (a) chiral sources, used as building blocks containing built-in stereocenters for target molecules; (b) chiral devices, employed as useful tools for enantioselective catalysts and auxiliaries; and (c) chiral inducers, applied to the generation of new stereocenters in a substrate-controlled manner [1][2][3][4][5][6][7]. The chiral inducer strategy is a highly efficient method to exploit advantages of both the chiral source and device approach at the same time.…”

Synthesis of 1,3,4-oxadiazole derivatives from α-amino acid and acyl hydrazides under thermal heating or microwave irradiation conditions

“…27,28 On the other hand, amino acids have emerged as important building blocks for the synthesis of a range of different compounds. [29][30][31] Moreover, the interest on the biological and medicinal properties of chalcogen amino acids has also been increasingly appreciated, mainly due to their antioxidant, 32 antitumor, 33 antimicrobial, 34 and antiviral 35 properties.…”