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.

Keywords

• antimicrobial
• heterocyclic compounds
• natural products
• pyrrolidinedione
• total synthesis