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

Autor: Atul A. Dhavan, Rahul D. Kaduskar, Loana Musso, Leonardo Scaglioni, Piera Anna Martino, Sabrina Dallavalle
Jazyk: angličtina
Rok vydání: 2016
Předmět:
Zdroj: Beilstein Journal of Organic Chemistry, Vol 12, Iss 1, Pp 1624-1628 (2016)
Druh dokumentu: article
ISSN: 1860-5397
DOI: 10.3762/bjoc.12.159
Popis: 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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