L- or D-glutamic acid-derived chiron: versatile chiral building blocks for enantioselective total syntheses of natural products

<p indent="0mm">The effective utilization of resource compounds stands as a pivotal choice in advancing sustainable organic synthesis. Employing chiral building blocks is imperative in the enantioselective synthesis of complex natural products and pharmaceutical molecules. Both natural L-glutamic acid and non-natural enantiomer D-glutamic acid are commercially available and cheap resource compounds. This review summarizes the applications of chiral building blocks (<italic>S</italic> or <italic>R</italic>)-3-hydroxyglutarimides and their derivatives, derived from L- or D-glutamic acid over the past <sc>15 years,</sc> in organic synthesis. These applications include the enantioselective synthesis of natural products such as awajanomycin, swainsonine, and FR901483, the construction of complex natural product core skeletons like sarain A and stemocurtisine, assembly of useful structural units such as 5-hydroxy-6-<italic>N</italic>-acylaminopiperidines, spiro-tricyclic moiety, bridged azatricyclic compounds, and oxygenated indolizidines, as well as a platform for developing synthetic methodologies. Additionally, the review offers a perspective on the prospective development of glutamic acid-derived chiral building blocks and their applications, exemplified by improved synthesis efficiency of 5-hydroxy-2-piperidone intermediates via direct amide transformations.