A strategic approach to [6,6]-bicyclic lactones: application towards the CD fragment of DHβE

We report an effective synthetic protocol to access [6,6]-bicyclic lactone moieties through a regio- and stereoselective intramolecular Mizoroki–Heck cross-coupling reaction followed by a 6π-electrocyclization. This method enabled the first synthesis of the elusive CD fragment of the Erythrina alkal...

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Detalles Bibliográficos
Autores principales: Jepsen, Tue Heesgaard, Glibstrup, Emil, Crestey, François, Jensen, Anders A, Kristensen, Jesper Langgaard
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2017
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5480346/
https://www.ncbi.nlm.nih.gov/pubmed/28684978
http://dx.doi.org/10.3762/bjoc.13.98
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author Jepsen, Tue Heesgaard
Glibstrup, Emil
Crestey, François
Jensen, Anders A
Kristensen, Jesper Langgaard
author_facet Jepsen, Tue Heesgaard
Glibstrup, Emil
Crestey, François
Jensen, Anders A
Kristensen, Jesper Langgaard
author_sort Jepsen, Tue Heesgaard
collection PubMed
description We report an effective synthetic protocol to access [6,6]-bicyclic lactone moieties through a regio- and stereoselective intramolecular Mizoroki–Heck cross-coupling reaction followed by a 6π-electrocyclization. This method enabled the first synthesis of the elusive CD fragment of the Erythrina alkaloid DHβE. Preliminary pharmacological evaluations support the notion that the key pharmacophores of DHβE are located in the A and B rings.
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spelling pubmed-54803462017-07-06 A strategic approach to [6,6]-bicyclic lactones: application towards the CD fragment of DHβE Jepsen, Tue Heesgaard Glibstrup, Emil Crestey, François Jensen, Anders A Kristensen, Jesper Langgaard Beilstein J Org Chem Full Research Paper We report an effective synthetic protocol to access [6,6]-bicyclic lactone moieties through a regio- and stereoselective intramolecular Mizoroki–Heck cross-coupling reaction followed by a 6π-electrocyclization. This method enabled the first synthesis of the elusive CD fragment of the Erythrina alkaloid DHβE. Preliminary pharmacological evaluations support the notion that the key pharmacophores of DHβE are located in the A and B rings. Beilstein-Institut 2017-05-22 /pmc/articles/PMC5480346/ /pubmed/28684978 http://dx.doi.org/10.3762/bjoc.13.98 Text en Copyright © 2017, Jepsen et al. https://creativecommons.org/licenses/by/4.0https://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/4.0), 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
Jepsen, Tue Heesgaard
Glibstrup, Emil
Crestey, François
Jensen, Anders A
Kristensen, Jesper Langgaard
A strategic approach to [6,6]-bicyclic lactones: application towards the CD fragment of DHβE
title A strategic approach to [6,6]-bicyclic lactones: application towards the CD fragment of DHβE
title_full A strategic approach to [6,6]-bicyclic lactones: application towards the CD fragment of DHβE
title_fullStr A strategic approach to [6,6]-bicyclic lactones: application towards the CD fragment of DHβE
title_full_unstemmed A strategic approach to [6,6]-bicyclic lactones: application towards the CD fragment of DHβE
title_short A strategic approach to [6,6]-bicyclic lactones: application towards the CD fragment of DHβE
title_sort strategic approach to [6,6]-bicyclic lactones: application towards the cd fragment of dhβe
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5480346/
https://www.ncbi.nlm.nih.gov/pubmed/28684978
http://dx.doi.org/10.3762/bjoc.13.98
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