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Synthesis 2021; 53(21): 3977-3990
DOI: 10.1055/a-1577-6085
DOI: 10.1055/a-1577-6085
short review
Synthesis of α-exo-Methylene-γ-butyrolactones: Recent Developments and Applications in Natural Product Synthesis
We thank the Swiss National Science Foundation (SNSF) for funding our efforts in the area of sesquiterpene lactone synthesis (Grant Nos. 169141, 188406) and the National Centres of Competence in Research (NCCR) Chemical Biology (Grant No. 185898).
Abstract
The α-exo-methylene-γ-butyrolactone moiety is present in a vast array of structurally diverse natural products and is often central to their biological activity. In this short review, we summarize new approaches to α-exo-methylene-γ-butyrolactones developed over the past decade as well as their applications in total synthesis.
1 Introduction
2 Approaches to α-exo-Methylene-γ-butyrolactones
2.1 Enantioselective Synthesis via Lactonization Approaches
2.2 Enantioselective Halolactonizations
2.3 Enantioselective Barbier-Type Allylation
2.4 C–H Insertion/Olefination Sequences
2.5 Alkene Cyclization
2.6 Strain-Driven Dyotropic Rearrangement
3 β-(Hydroxymethylalkyl)-α-exo-methylene-γ-butyrolactones
4 Applications in Total Synthesis
4.1 Sesquiterpene Lactones
4.2 Lignans
4.3 Other Monocyclic Natural Products
4.4 Choice of Methodology in Recent Total Syntheses
5 Summary and Outlook
Key words
natural products - α-exo-methylene-γ-butyrolactones - total synthesis - sesquiterpene lactones - lignansPublication History
Received: 07 July 2021
Accepted after revision: 03 August 2021
Accepted Manuscript online:
03 August 2021
Article published online:
01 October 2021
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