Abstract
γ-Butyrolactone, a five-membered lactone moiety, is one of the privileged structures of diverse natural products and biologically active small molecules. Because of their broad spectrum of biological and pharmacological activities, synthetic methods for γ-butyrolactones have received significant attention from synthetic and medicinal chemists for decades. Recently, new developments and improvements in traditional methods have been reported by considering synthetic efficiency, feasibility, and green chemistry. In this review, the pharmacological activities of natural and synthetic γ-butyrolactones are described, including their structures and bioassay methods. Mainly, we summarize recent advances, occurring during the past decade, in the construction of γ-butyrolactone classified based on the bond formation in γ-butyrolactone between (i) C5-O1 bond, (ii) C4-C5 and C2-O1 bonds, (iii) C3-C4 and C2-O1 bonds, (iv) C3-C4 and C5-O1 bonds, (v) C2-C3 and C2-O1 bonds, (vi) C3-C4 bond, and (vii) C2-O1 bond. In addition, the application to the total synthesis of natural products bearing γ-butyrolactone scaffolds is described.
Highlights
Asymmetric synthesis of α-exo-methylene γ-butyrolactone via chromium-catalyzed tion and lactonization and total synthesis of (+)-methylenolactocin
Another example of γ-butyrolactone synthesis mediated by photoredox catalysis is atom-transfer radical addition (ATRA), which was reported by Kokotos and colleagues in
Formationreaction of α,β-unsatusentative reactions in this class is the cyclopropanol cross-coupling reactio rated enone byproducts, which are normally causedring-opening by β-hydrideoxidants, eliminationre-of the mediated by diverse transition metal catalysts or single-electron transferring mediated by diverse transition metal catalysts or single-electron transferring Dai oxidants, r metallo-homoenolate
Summary
Abstract: γ-Butyrolactone, a five-membered lactone moiety, is one of the privileged structures of diverse natural products and biologically active small molecules. Because of their broad spectrum of biological and pharmacological activities, synthetic methods for γ-butyrolactones have received significant attention from synthetic and medicinal chemists for decades. The pharmacological activities of natural and synthetic γ-butyrolactones are described, including their structures and bioassay methods. We summarize recent advances, occurring during the past decade, in the construction of γ-butyrolactone classified based on the bond formation in γ-butyrolactone between (i) C5-O1 bond, (ii) C4-C5 and. The application to the total synthesis of natural products bearing γ-butyrolactone scaffolds is described.
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