Abstract
Chiral pool α-amino acids have been used as powerful tools for the total synthesis of structurally diverse natural products. Some common naturally occurring α-amino acids are readily available in both enantiomerically pure forms. The applications of the chiral pool in asymmetric synthesis can be categorized prudently as chiral sources, devices, and inducers. This review specifically examines recent advances in substrate-controlled asymmetric reactions induced by the chirality of α-amino acid templates in natural product synthesis research and related areas.
Highlights
The chiral pool approach is highly attractive in the asymmetric total synthesis of bioactive natural products with diverse and complex architectures [1,2]
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 specific aim of this review is to present useful applications of enantiomerically enriched α-amino acids as substrate-controlled asymmetric inducers in natural product synthesis from 2011 to May 2016
Summary
The chiral pool approach is highly attractive in the asymmetric total synthesis of bioactive natural products with diverse and complex architectures [1,2]. 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] They include enantiomerically enriched species that can be synthetically transformed into the desired target molecules.
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