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γ-Hydroxy Amides from Tartaric Acid: Versatile Chiral Building Blocks for the Total Synthesis of Natural Products

Nanda, LN and Shruthi, KS and Prasad, KR (2021) γ-Hydroxy Amides from Tartaric Acid: Versatile Chiral Building Blocks for the Total Synthesis of Natural Products. In: Chemical Record, 21 (8). pp. 1957-1967.

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Official URL: https://doi.org/10.1002/tcr.202100129


“Chiral pool” compounds possessing well defined stereocenters and suitable functionality serve as excellent building blocks for the synthesis of natural products and therapeutically important compounds. Tartaric acid is a C2-symmetric molecule available in both enantiomeric forms. It was extensively utilized in the synthesis of privileged chiral ligands/catalysts such as TADDOLs, and as a start point in the synthesis of plethora of compounds. The advent of several new C−C bond forming reactions offers opportunity for the development of novel synthetic strategies based on chiral pool compounds. We found that the desymmetrization of the bis-dimethyl amide/Weinreb amide derived from tartaric acid can be accomplished by controlled addition of Grignard /organolithium reagents leading to the mono keto amides, the reduction of which affords the γ-hydroxy amides. This account describes our research efforts of more than a decade on the synthesis and application of diverse γ-hydroxy amides derived from tartaric acid in the total synthesis of structurally simple to complex bio-active natural products.

Item Type: Journal Article
Publication: Chemical Record
Publisher: John Wiley and Sons Inc
Additional Information: The copyright for this article belongs to John Wiley and Sons Inc.
Keywords: amide; biological product; lactone; ligand; pyrone derivative; tartaric acid, catalysis; chemistry; stereoisomerism; synthesis, Amides; Biological Products; Catalysis; Lactones; Ligands; Pyrones; Stereoisomerism; Tartrates
Department/Centre: Division of Chemical Sciences > Organic Chemistry
Date Deposited: 27 Mar 2023 06:26
Last Modified: 27 Mar 2023 06:26
URI: https://eprints.iisc.ac.in/id/eprint/81063

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