Department of Chemistry, Indian Institute of Technology Kharagpur, Kharagpur, 721302, India.
Org Biomol Chem. 2021 Sep 14;19(34):7298-7332. doi: 10.1039/d1ob00875g. Epub 2021 Aug 13.
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.
γ-丁烯内酯是许多天然存在的化合物中基本的骨架,具有巨大的生物活性。γ-丁烯内酯也已被证明是天然产物全合成中有用的合成中间体。多年来,已经分离出许多具有环外γ-δ 不饱和的γ-丁烯内酯天然产物,这些天然产物通常被称为γ-烷基丁烯内酯。考虑到光学活性γ-丁烯内酯具有不同的生物学特征和广泛的结构多样性,因此,开发用于组装这些具有挑战性的支架的合成策略引起了合成化学家的广泛关注。在本报告中,将简要讨论这些分子的分离、生物发生和当前最先进的合成方法。本报告旨在重点介绍 2010-2020 年 γ-丁烯内酯的合成策略,特别关注γ-烷基丁烯内酯及相关分子。金属介导的催化转化和有机催化是两种广泛用于获得此类分子的主要反应类型。还考虑了报道的程序的机理考虑、对映选择性合成和实际应用。