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

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 i...

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Autores principales: Dhavan, Atul A, Kaduskar, Rahul D, Musso, Loana, Scaglioni, Leonardo, Martino, Piera Anna, Dallavalle, Sabrina
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2016
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4979754/
https://www.ncbi.nlm.nih.gov/pubmed/27559415
http://dx.doi.org/10.3762/bjoc.12.159
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author Dhavan, Atul A
Kaduskar, Rahul D
Musso, Loana
Scaglioni, Leonardo
Martino, Piera Anna
Dallavalle, Sabrina
author_facet Dhavan, Atul A
Kaduskar, Rahul D
Musso, Loana
Scaglioni, Leonardo
Martino, Piera Anna
Dallavalle, Sabrina
author_sort Dhavan, Atul A
collection PubMed
description 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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spelling pubmed-49797542016-08-24 Total synthesis of leopolic acid A, a natural 2,3-pyrrolidinedione with antimicrobial activity Dhavan, Atul A Kaduskar, Rahul D Musso, Loana Scaglioni, Leonardo Martino, Piera Anna Dallavalle, Sabrina Beilstein J Org Chem Full Research Paper 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. Beilstein-Institut 2016-07-29 /pmc/articles/PMC4979754/ /pubmed/27559415 http://dx.doi.org/10.3762/bjoc.12.159 Text en Copyright © 2016, Dhavan et al. https://creativecommons.org/licenses/by/2.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Full Research Paper
Dhavan, Atul A
Kaduskar, Rahul D
Musso, Loana
Scaglioni, Leonardo
Martino, Piera Anna
Dallavalle, Sabrina
Total synthesis of leopolic acid A, a natural 2,3-pyrrolidinedione with antimicrobial activity
title Total synthesis of leopolic acid A, a natural 2,3-pyrrolidinedione with antimicrobial activity
title_full Total synthesis of leopolic acid A, a natural 2,3-pyrrolidinedione with antimicrobial activity
title_fullStr Total synthesis of leopolic acid A, a natural 2,3-pyrrolidinedione with antimicrobial activity
title_full_unstemmed Total synthesis of leopolic acid A, a natural 2,3-pyrrolidinedione with antimicrobial activity
title_short Total synthesis of leopolic acid A, a natural 2,3-pyrrolidinedione with antimicrobial activity
title_sort total synthesis of leopolic acid a, a natural 2,3-pyrrolidinedione with antimicrobial activity
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4979754/
https://www.ncbi.nlm.nih.gov/pubmed/27559415
http://dx.doi.org/10.3762/bjoc.12.159
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