Annulative coupling of α-substituted acrylic acids and sulfoxonium ylides: easy access to bioactive γ-butyrolactones

Abstract

We present a straightforward, catalyst- and additive-free method for synthesizing keto γ-butyrolactones using readily available β-keto sulfoxonium ylides and acrylic acids. This robust approach demonstrates exceptional compatibility with various functional groups on β-keto sulfoxonium ylides and α-substituted acrylic acids, resulting in good to high yields of the anticipated products. Moreover, the practicality of this approach was validated through large-scale reactions and the successful conversion of some synthesized derivatives into bioactive natural products, including L-factor, muricatacin, and cytosporanone A. © 2024 The Royal Society of Chemistry.