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Beilstein-Institut, Beilstein Journal of Organic Chemistry, (12), p. 1624-1628, 2016

DOI: 10.3762/bjoc.12.159

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

Journal article published in 2016 by Atul A. Dhavan, Rahul D. Kaduskar, Loana Musso, Leonardo Scaglioni, Piera Anna Martino, Sabrina Dallavalle ORCID
This paper is made freely available by the publisher.
This paper is made freely available by the publisher.

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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.