Title:Pyroglutamic Acid and its Derivatives: The Privileged Precursors for the Asymmetric Synthesis of Bioactive Natural Products
VOLUME: 17 ISSUE: 6
Author(s):Sharad Kumar Panday*
Affiliation:Department of Applied Chemistry, Faculty of Engineering & Technology, M.J.P. Rohilkhand University, Bareilly, U.P.
Keywords:Asymmetric synthesis, bioactive molecules, natural products, privileged asymmetric precursor, pyroglutamic acid
derivatives, pyroglutamic acid.
Abstract:Pyroglutamic acid is one of the privileged asymmetric precursors for the synthesis of a variety
of molecules such as Angiotensin-Converting Enzyme (ACE) inhibitors, angiotensin II receptor
subtypes (AT-1 receptor antagonists), as well as bioactive natural products. Starting with primary reports
in 1980’s, last almost four decades has witnessed a rapid overgrowth of publications using pyroglutamic
acid as a preferred asymmetric precursor and these have been well documented. Pyroglutamic
acid has two differential carbonyl groups a lactam carbonyl and a carboxylic functionality
along with an NH group, and all of these functionalities can be further derivatized/ transformed and
in turn opened avenues for the synthesis of variety of molecules. Derived easily from glutamic acid
by internal cyclization, pyroglutamic acid offers a cheap and very good source of chirality and has
provided an important tool for the synthesis of natural products/intermediates to natural products.
Herein, we wish to describe the exploitation of the chemistry of pyroglutamic acid and its derivatives
in the asymmetric synthesis of natural products establishing its versatility as a privileged asymmetric
precursor.