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Total synthesis of leopolic acid A, a natural 2,3-pyrrolidinedione with antimicrobial activity. | LitMetric

Total synthesis of leopolic acid A, a natural 2,3-pyrrolidinedione with antimicrobial activity.

Beilstein J Org Chem

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.

Published: August 2016

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.

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Source
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC4979754PMC
http://dx.doi.org/10.3762/bjoc.12.159DOI Listing

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