Total Synthesis of Fellutamide B and Deoxy-Fellutamides B, C, and D

The total syntheses of the marine-derived lipopeptide natural product fellutamide B and deoxy-fellutamides B, C, and D are reported. These compounds were accessed through a novel solid-phase synthetic strategy using Weinreb amide-derived resin. As part of the synthesis, a new enantioselective route...

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Autores principales: Giltrap, Andrew M., Cergol, Katie M., Pang, Angel, Britton, Warwick J., Payne, Richard J.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2013
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3736429/
https://www.ncbi.nlm.nih.gov/pubmed/23880930
http://dx.doi.org/10.3390/md11072382
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author Giltrap, Andrew M.
Cergol, Katie M.
Pang, Angel
Britton, Warwick J.
Payne, Richard J.
author_facet Giltrap, Andrew M.
Cergol, Katie M.
Pang, Angel
Britton, Warwick J.
Payne, Richard J.
author_sort Giltrap, Andrew M.
collection PubMed
description The total syntheses of the marine-derived lipopeptide natural product fellutamide B and deoxy-fellutamides B, C, and D are reported. These compounds were accessed through a novel solid-phase synthetic strategy using Weinreb amide-derived resin. As part of the synthesis, a new enantioselective route to (3R)-hydroxy lauric acid was developed utilizing a Brown allylation reaction followed by an oxidative cleavage-oxidation sequence as the key steps. The activity of these natural products, and natural product analogues was also assessed against Mycobacterium tuberculosis in vitro.
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spelling pubmed-37364292013-08-07 Total Synthesis of Fellutamide B and Deoxy-Fellutamides B, C, and D Giltrap, Andrew M. Cergol, Katie M. Pang, Angel Britton, Warwick J. Payne, Richard J. Mar Drugs Article The total syntheses of the marine-derived lipopeptide natural product fellutamide B and deoxy-fellutamides B, C, and D are reported. These compounds were accessed through a novel solid-phase synthetic strategy using Weinreb amide-derived resin. As part of the synthesis, a new enantioselective route to (3R)-hydroxy lauric acid was developed utilizing a Brown allylation reaction followed by an oxidative cleavage-oxidation sequence as the key steps. The activity of these natural products, and natural product analogues was also assessed against Mycobacterium tuberculosis in vitro. MDPI 2013-07-08 /pmc/articles/PMC3736429/ /pubmed/23880930 http://dx.doi.org/10.3390/md11072382 Text en © 2013 by the authors; licensee MDPI, Basel, Switzerland. http://creativecommons.org/licenses/by/3.0/ This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/3.0/).
spellingShingle Article
Giltrap, Andrew M.
Cergol, Katie M.
Pang, Angel
Britton, Warwick J.
Payne, Richard J.
Total Synthesis of Fellutamide B and Deoxy-Fellutamides B, C, and D
title Total Synthesis of Fellutamide B and Deoxy-Fellutamides B, C, and D
title_full Total Synthesis of Fellutamide B and Deoxy-Fellutamides B, C, and D
title_fullStr Total Synthesis of Fellutamide B and Deoxy-Fellutamides B, C, and D
title_full_unstemmed Total Synthesis of Fellutamide B and Deoxy-Fellutamides B, C, and D
title_short Total Synthesis of Fellutamide B and Deoxy-Fellutamides B, C, and D
title_sort total synthesis of fellutamide b and deoxy-fellutamides b, c, and d
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3736429/
https://www.ncbi.nlm.nih.gov/pubmed/23880930
http://dx.doi.org/10.3390/md11072382
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