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γ ‐Hydroxy Amides from Tartaric Acid: Versatile Chiral Building Blocks for the Total Synthesis of Natural Products
Author(s) -
Nanda Laxmi Narayan,
Shruthi Kodambahalli S.,
Prasad Kavirayani R.
Publication year - 2021
Publication title -
the chemical record
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.61
H-Index - 78
eISSN - 1528-0691
pISSN - 1527-8999
DOI - 10.1002/tcr.202100129
Subject(s) - stereocenter , tartaric acid , desymmetrization , amide , chemistry , enantiomer , combinatorial chemistry , reagent , organic chemistry , total synthesis , enantioselective synthesis , catalysis , citric acid
“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 C 2 ‐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.