Total Synthesis of Berkeleylactone A.

Anti-Bacterial Agents / chemical synthesis Crystallography, X-Ray Macrolides / chemical synthesis Methicillin-Resistant Staphylococcus aureus / drug effects Microbial Sensitivity Tests Models, Molecular Molecular Structure Stereoisomerism

Journal

The Journal of organic chemistry
ISSN: 1520-6904
Titre abrégé: J Org Chem
Pays: United States
ID NLM: 2985193R

Informations de publication

Date de publication:
07 06 2019
Historique:
pubmed: 14 5 2019
medline: 8 7 2020
entrez: 14 5 2019
Statut: ppublish

Résumé

The first total synthesis of the potent antibiotic berkeleylactone A is described in 10 steps with an overall yield of 9.5%. A key step of our concise route is a late-stage, highly diastereoselective, sulfa-Michael addition. The 16-membered macrocyclic lactone was formed via ring closing metathesis and subsequent chemoselective reduction. The absolute stereochemical configuration was confirmed by single-crystal X-ray analysis. Synthetic berkeleylactone A was tested against several methicillin-resistant Staphylococcus aureus strains, and its potent antibacterial activity was verified.

Identifiants

DOI: 10.1021/acs.joc.9b00850 PMID: 31081630
pubmed: 31081630
doi: 10.1021/acs.joc.9b00850
doi:

Substances chimiques

Anti-Bacterial Agents 0
Macrolides 0
berkeleylactone A 0

Types de publication

Journal Article Research Support, Non-U.S. Gov't

Langues

eng

Sous-ensembles de citation

IM

Pagination

7159-7165

Auteurs

Branislav Ferko (B)

Faculty of Chemical and Food Technology , Slovak University of Technology , Radlinskeho 9 , 81237 Bratislava , Slovakia.
Department of Chemistry , University of Oxford, Chemistry Research Laboratory , Oxford OX1 3TA , U.K.

Marián Zeman (M)

Faculty of Chemical and Food Technology , Slovak University of Technology , Radlinskeho 9 , 81237 Bratislava , Slovakia.

Michele Formica (M)

Department of Chemistry , University of Oxford, Chemistry Research Laboratory , Oxford OX1 3TA , U.K.

Sebastián Veselý (S)

Faculty of Chemical and Food Technology , Slovak University of Technology , Radlinskeho 9 , 81237 Bratislava , Slovakia.

Jana Doháňošová (J)

Faculty of Chemical and Food Technology , Slovak University of Technology , Radlinskeho 9 , 81237 Bratislava , Slovakia.

Ján Moncol (J)

Faculty of Chemical and Food Technology , Slovak University of Technology , Radlinskeho 9 , 81237 Bratislava , Slovakia.
ORCID: 0000-0003-2153-9753

Petra Olejníková (P)

Faculty of Chemical and Food Technology , Slovak University of Technology , Radlinskeho 9 , 81237 Bratislava , Slovakia.

Dušan Berkeš (D)

Faculty of Chemical and Food Technology , Slovak University of Technology , Radlinskeho 9 , 81237 Bratislava , Slovakia.

Pavol Jakubec (P)

Faculty of Chemical and Food Technology , Slovak University of Technology , Radlinskeho 9 , 81237 Bratislava , Slovakia.
ORCID: 0000-0001-8872-3817

Darren J Dixon (DJ)

Department of Chemistry , University of Oxford, Chemistry Research Laboratory , Oxford OX1 3TA , U.K.
ORCID: 0000-0003-2456-5236

Ol'ga Caletková (O)

Faculty of Chemical and Food Technology , Slovak University of Technology , Radlinskeho 9 , 81237 Bratislava , Slovakia.
ORCID: 0000-0001-6296-7266

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Classifications MeSH

questionsmedicales.fr › Actions chimiques et utilisations › Actions pharmacologiques › Utilisations thérapeutiques › Anti-infectieux › Antibactériens › Total Synthesis of Berkeleylactone A.
questionsmedicales.fr › Techniques d'investigation › Techniques de chimie analytique › Cristallographie aux rayons X › Total Synthesis of Berkeleylactone A.
questionsmedicales.fr › Composés polycycliques › Composés macrocycliques › Polycétides › Macrolides › Total Synthesis of Berkeleylactone A.
questionsmedicales.fr › Bactéries › Bactéries à Gram positif › Cocci à Gram positif › Staphylococcaceae › Staphylococcus › Staphylococcus aureus › Staphylococcus aureus résistant à la méticilline › Total Synthesis of Berkeleylactone A.
questionsmedicales.fr › Techniques d'investigation › Évaluation préclinique de médicament › Tests de sensibilité microbienne › Total Synthesis of Berkeleylactone A.
questionsmedicales.fr › Techniques d'investigation › Modèles théoriques › Modèles moléculaires › Total Synthesis of Berkeleylactone A.
questionsmedicales.fr › Phénomènes chimiques › Structure moléculaire › Total Synthesis of Berkeleylactone A.
questionsmedicales.fr › Phénomènes chimiques › Phénomènes de chimie organique › Isomérie › Stéréoisomérie › Total Synthesis of Berkeleylactone A.