Recent reports on the synthesis of γ-butenolide, γ-alkylidenebutenolide frameworks, and related natural products.

Abstract

γ-Butenolides are fundamental frameworks found in many naturally occurring compounds, and they exhibit tremendous biological activities. γ-Butenolides also have proven their potential as useful synthetic intermediates in the total synthesis of natural compounds. Over the years, many γ-butenolide natural products have been isolated, having exocyclic γ-δ unsaturation in their structure. These natural products are collectively referred to as γ-alkylidenebutenolides. Considering the different biological profiles and wide-ranging structural diversity of the optically active γ-butenolide, the development of synthetic strategies for assembling such challenging scaffolds has attracted significant attention from synthetic chemists in recent times. In this report, a brief discussion will be provided to address isolation, biogenesis, and current state-of-the-art synthetic protocols for such molecules. This report aims to focus on synthetic strategies for γ-butenolides from 2010-2020 with a particular emphasis on γ-alkylidenebutenolides and related molecules. Metal-mediated catalytic transformation and organocatalysis are the two main reaction types that have been widely used to access such molecules. Mechanistic considerations, enantioselective synthesis, and practical applications of the reported procedures are also taken into consideration.