A cross-metathesis approach to novel pantothenamide derivatives

Pantothenamides are known for their in vitro antimicrobial activity. Our group has previously reported a new stereoselective route to access derivatives modified at the geminal dimethyl moiety. This route however fails in the addition of large substituents. Here we report a new synthetic route that...

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Detalles Bibliográficos
Autores principales: Guan, Jinming, Hachey, Matthew, Puri, Lekha, Howieson, Vanessa, Saliba, Kevin J, Auclair, Karine
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/PMC4902030/
https://www.ncbi.nlm.nih.gov/pubmed/27340487
http://dx.doi.org/10.3762/bjoc.12.95
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author Guan, Jinming
Hachey, Matthew
Puri, Lekha
Howieson, Vanessa
Saliba, Kevin J
Auclair, Karine
author_facet Guan, Jinming
Hachey, Matthew
Puri, Lekha
Howieson, Vanessa
Saliba, Kevin J
Auclair, Karine
author_sort Guan, Jinming
collection PubMed
description Pantothenamides are known for their in vitro antimicrobial activity. Our group has previously reported a new stereoselective route to access derivatives modified at the geminal dimethyl moiety. This route however fails in the addition of large substituents. Here we report a new synthetic route that exploits the known allyl derivative, allowing for the installation of larger groups via cross-metathesis. The method was applied in the synthesis of a new pantothenamide with improved stability in human blood.
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spelling pubmed-49020302016-06-23 A cross-metathesis approach to novel pantothenamide derivatives Guan, Jinming Hachey, Matthew Puri, Lekha Howieson, Vanessa Saliba, Kevin J Auclair, Karine Beilstein J Org Chem Full Research Paper Pantothenamides are known for their in vitro antimicrobial activity. Our group has previously reported a new stereoselective route to access derivatives modified at the geminal dimethyl moiety. This route however fails in the addition of large substituents. Here we report a new synthetic route that exploits the known allyl derivative, allowing for the installation of larger groups via cross-metathesis. The method was applied in the synthesis of a new pantothenamide with improved stability in human blood. Beilstein-Institut 2016-05-13 /pmc/articles/PMC4902030/ /pubmed/27340487 http://dx.doi.org/10.3762/bjoc.12.95 Text en Copyright © 2016, Guan 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
Guan, Jinming
Hachey, Matthew
Puri, Lekha
Howieson, Vanessa
Saliba, Kevin J
Auclair, Karine
A cross-metathesis approach to novel pantothenamide derivatives
title A cross-metathesis approach to novel pantothenamide derivatives
title_full A cross-metathesis approach to novel pantothenamide derivatives
title_fullStr A cross-metathesis approach to novel pantothenamide derivatives
title_full_unstemmed A cross-metathesis approach to novel pantothenamide derivatives
title_short A cross-metathesis approach to novel pantothenamide derivatives
title_sort cross-metathesis approach to novel pantothenamide derivatives
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4902030/
https://www.ncbi.nlm.nih.gov/pubmed/27340487
http://dx.doi.org/10.3762/bjoc.12.95
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