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.
Total synthesis of leopolic acid A, a natural 2,3-pyrrolidinedione with antimicrobial activity / A.A. Dhavan, R.D. Kaduskar, L. Musso, L. Scaglioni, P.A. Martino, S. Dallavalle. - In: BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY. - ISSN 1860-5397. - 12(2016 Jul 29), pp. 1624-1628.
Total synthesis of leopolic acid A, a natural 2,3-pyrrolidinedione with antimicrobial activity
R.D. KaduskarSecondo
;L. Musso;L. Scaglioni;P.A. MartinoPenultimo
;S. DallavalleUltimo
2016
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.File | Dimensione | Formato | |
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