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 - lignans
