Issue 34, 2021

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.

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

Article information

Article type
Review Article
Submitted
05 may 2021
Accepted
29 iyl 2021
First published
29 iyl 2021

Org. Biomol. Chem., 2021,19, 7298-7332

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

S. Chatterjee, R. Sahoo and S. Nanda, Org. Biomol. Chem., 2021, 19, 7298 DOI: 10.1039/D1OB00875G

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements