title: Total synthesis of leopolic acid A, a natural 2,3-pyrrolidinedione with antimicrobial activity.
abstract: The first total synthesis of leopolic acid A, a fungal metabolite with a rare 2,3-pyrrolidinedione nucleus linked to an ureido dipeptide, was designed and carried out. Crucial steps for the strategy include a Dieckmann cyclization to obtain the 2,3-pyrrolidinedione ring and a Wittig olefination to install the polymethylene chain. An oxazolidinone-containing leopolic acid A analogue was also synthesized. The antibacterial activity showed by both compounds suggests that they could be considered as promising candidates for future developments.
authors: Department of Food, Environmental and Nutritional Sciences, Division of Chemistry and Molecular Biology, Università degli Studi di Milano, via Celoria 2, I-20133 Milano, Italy.
authors: Atul A
authors: AA
authors: Dhavan
authors: Department of Food, Environmental and Nutritional Sciences, Division of Chemistry and Molecular Biology, Università degli Studi di Milano, via Celoria 2, I-20133 Milano, Italy.
authors: Rahul D
authors: RD
authors: Kaduskar
authors: Department of Food, Environmental and Nutritional Sciences, Division of Chemistry and Molecular Biology, Università degli Studi di Milano, via Celoria 2, I-20133 Milano, Italy.
authors: Loana
authors: L
authors: Musso
authors: Department of Food, Environmental and Nutritional Sciences, Division of Chemistry and Molecular Biology, Università degli Studi di Milano, via Celoria 2, I-20133 Milano, Italy.
authors: Leonardo
authors: L
authors: Scaglioni
authors: Department of Veterinary Medicine - Microbiology and Immunology, Università degli Studi di Milano, via Celoria 10, I-20133 Milano, Italy.
authors: Piera Anna
authors: PA
authors: Martino
authors: Department of Food, Environmental and Nutritional Sciences, Division of Chemistry and Molecular Biology, Università degli Studi di Milano, via Celoria 2, I-20133 Milano, Italy.
authors: Sabrina
authors: S
authors: Dallavalle
keywords: antimicrobial; heterocyclic compounds; natural products; pyrrolidinedione; total synthesis