Total Synthesis of a Natural 2,3-Pyrrolidinedione

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  • Published: 09 August 2016
  • Copyright: Wiley-VCH Verlag GmbH & Co. KGaA
  • Source / Publisher: Beilstein Journal of Organic Chemistry
thumbnail image: Total Synthesis of a Natural 2,3-Pyrrolidinedione

Sabrina Dallavalle and colleagues, Università degli Studi di Milano, Italy, report the first total synthesis of leopolic acid A, a fungal metabolite with antimicrobial activity and with a rare 2,3-pyrrolidinedione nucleus linked to an ureido dipeptide.

Crucial steps of the 11-step synthesis include a Dieckmann cyclization to obtain the 2,3-pyrrolidinedione ring and a Wittig olefination to install the polymethylene chain.

In adition, the team synthesized an oxazolidinone-containing leopolic acid A. Both compounds showed antibacterial activity.

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