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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.

SUBMITTER: Dhavan AA

PROVIDER: S-EPMC4979754 | biostudies-literature | 2016

REPOSITORIES: biostudies-literature

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

Dhavan Atul A AA Kaduskar Rahul D RD Musso Loana L Scaglioni Leonardo L Martino Piera Anna PA Dallavalle Sabrina S

Beilstein journal of organic chemistry 20160729

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 ...[more]

PMID: 27559415

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