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

Chem Commun (Camb)

Department of Chemistry, Institute of Science, Banaras Hindu University, Varanasi 221005, India.

Published: August 2024

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.

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Source
http://dx.doi.org/10.1039/d4cc03187cDOI Listing

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