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Towards the Total Synthesis of Pl-3: Preparation of the Eastern Fragment through a Diastereoselective SmI(2)-Mediated Reformatsky Reaction
The jatrophane diterpene Pl-3, isolated in 2003 from Euphorbia platyphyllos, is a structurally complex natural product with highly promising biological properties that include pronounced antiproliferative activity and the inhibition of the efflux-pump activity of multidrug resistance p-glycoprotein....
Autores principales: | , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
WILEY-VCH Verlag
2013
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3654569/ https://www.ncbi.nlm.nih.gov/pubmed/23687456 http://dx.doi.org/10.1002/ejoc.201300148 |
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author | Fürst, Rita Lentsch, Christoph Rinner, Uwe |
author_facet | Fürst, Rita Lentsch, Christoph Rinner, Uwe |
author_sort | Fürst, Rita |
collection | PubMed |
description | The jatrophane diterpene Pl-3, isolated in 2003 from Euphorbia platyphyllos, is a structurally complex natural product with highly promising biological properties that include pronounced antiproliferative activity and the inhibition of the efflux-pump activity of multidrug resistance p-glycoprotein. Herein, the synthesis of the eastern fragment of Pl-3 is outlined. The target compound is synthesized in nine synthetic operations in good overall yield, starting from readily available d-ribose. The key step in the preparation of the eastern part of Pl-3 is a diastereoselective SmI(2)-mediated Reformatsky reaction. The proposed route is highly flexible and could also be applied to the synthesis of structurally related jatrophane diterpenes. |
format | Online Article Text |
id | pubmed-3654569 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2013 |
publisher | WILEY-VCH Verlag |
record_format | MEDLINE/PubMed |
spelling | pubmed-36545692013-05-17 Towards the Total Synthesis of Pl-3: Preparation of the Eastern Fragment through a Diastereoselective SmI(2)-Mediated Reformatsky Reaction Fürst, Rita Lentsch, Christoph Rinner, Uwe European J Org Chem Short Communications The jatrophane diterpene Pl-3, isolated in 2003 from Euphorbia platyphyllos, is a structurally complex natural product with highly promising biological properties that include pronounced antiproliferative activity and the inhibition of the efflux-pump activity of multidrug resistance p-glycoprotein. Herein, the synthesis of the eastern fragment of Pl-3 is outlined. The target compound is synthesized in nine synthetic operations in good overall yield, starting from readily available d-ribose. The key step in the preparation of the eastern part of Pl-3 is a diastereoselective SmI(2)-mediated Reformatsky reaction. The proposed route is highly flexible and could also be applied to the synthesis of structurally related jatrophane diterpenes. WILEY-VCH Verlag 2013-04 2013-03-07 /pmc/articles/PMC3654569/ /pubmed/23687456 http://dx.doi.org/10.1002/ejoc.201300148 Text en Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim http://creativecommons.org/licenses/by/2.5/ Re-use of this article is permitted in accordance with the Creative Commons Deed, Attribution 2.5, which does not permit commercial exploitation. |
spellingShingle | Short Communications Fürst, Rita Lentsch, Christoph Rinner, Uwe Towards the Total Synthesis of Pl-3: Preparation of the Eastern Fragment through a Diastereoselective SmI(2)-Mediated Reformatsky Reaction |
title | Towards the Total Synthesis of Pl-3: Preparation of the Eastern Fragment through a Diastereoselective SmI(2)-Mediated Reformatsky Reaction |
title_full | Towards the Total Synthesis of Pl-3: Preparation of the Eastern Fragment through a Diastereoselective SmI(2)-Mediated Reformatsky Reaction |
title_fullStr | Towards the Total Synthesis of Pl-3: Preparation of the Eastern Fragment through a Diastereoselective SmI(2)-Mediated Reformatsky Reaction |
title_full_unstemmed | Towards the Total Synthesis of Pl-3: Preparation of the Eastern Fragment through a Diastereoselective SmI(2)-Mediated Reformatsky Reaction |
title_short | Towards the Total Synthesis of Pl-3: Preparation of the Eastern Fragment through a Diastereoselective SmI(2)-Mediated Reformatsky Reaction |
title_sort | towards the total synthesis of pl-3: preparation of the eastern fragment through a diastereoselective smi(2)-mediated reformatsky reaction |
topic | Short Communications |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3654569/ https://www.ncbi.nlm.nih.gov/pubmed/23687456 http://dx.doi.org/10.1002/ejoc.201300148 |
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