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Cascade Metathesis Reactions for the Synthesis of Taxane and Isotaxane Derivatives

Tricyclic isotaxane and taxane derivatives have been synthesized by a very efficient cascade ring‐closing dienyne metathesis (RCDEYM) reaction, which formed the A and B rings in one operation. When the alkyne is present at C13 (with no neighboring gem‐dimethyl group), the RCEDYM reaction leads to 14...

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Autores principales: Ma, Cong, Letort, Aurélien, Aouzal, Rémi, Wilkes, Antonia, Maiti, Gourhari, Farrugia, Louis J., Ricard, Louis, Prunet, Joëlle
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2016
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4982030/
https://www.ncbi.nlm.nih.gov/pubmed/27062670
http://dx.doi.org/10.1002/chem.201600592
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author Ma, Cong
Letort, Aurélien
Aouzal, Rémi
Wilkes, Antonia
Maiti, Gourhari
Farrugia, Louis J.
Ricard, Louis
Prunet, Joëlle
author_facet Ma, Cong
Letort, Aurélien
Aouzal, Rémi
Wilkes, Antonia
Maiti, Gourhari
Farrugia, Louis J.
Ricard, Louis
Prunet, Joëlle
author_sort Ma, Cong
collection PubMed
description Tricyclic isotaxane and taxane derivatives have been synthesized by a very efficient cascade ring‐closing dienyne metathesis (RCDEYM) reaction, which formed the A and B rings in one operation. When the alkyne is present at C13 (with no neighboring gem‐dimethyl group), the RCEDYM reaction leads to 14,15‐isotaxanes 16 a,b and 18 b with the gem‐dimethyl group on the A ring. If the alkyne is at the C11 position (and thus flanked by a gem‐dimethyl group), RCEDYM reaction only proceeds in the presence of a trisubstituted olefin at C13, which disfavors the competing diene ring‐closing metathesis reaction, to give the tricyclic core of Taxol 44.
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spelling pubmed-49820302016-08-26 Cascade Metathesis Reactions for the Synthesis of Taxane and Isotaxane Derivatives Ma, Cong Letort, Aurélien Aouzal, Rémi Wilkes, Antonia Maiti, Gourhari Farrugia, Louis J. Ricard, Louis Prunet, Joëlle Chemistry Full Papers Tricyclic isotaxane and taxane derivatives have been synthesized by a very efficient cascade ring‐closing dienyne metathesis (RCDEYM) reaction, which formed the A and B rings in one operation. When the alkyne is present at C13 (with no neighboring gem‐dimethyl group), the RCEDYM reaction leads to 14,15‐isotaxanes 16 a,b and 18 b with the gem‐dimethyl group on the A ring. If the alkyne is at the C11 position (and thus flanked by a gem‐dimethyl group), RCEDYM reaction only proceeds in the presence of a trisubstituted olefin at C13, which disfavors the competing diene ring‐closing metathesis reaction, to give the tricyclic core of Taxol 44. John Wiley and Sons Inc. 2016-04-08 2016-05-10 /pmc/articles/PMC4982030/ /pubmed/27062670 http://dx.doi.org/10.1002/chem.201600592 Text en © 2016 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution (http://creativecommons.org/licenses/by/4.0/) License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
spellingShingle Full Papers
Ma, Cong
Letort, Aurélien
Aouzal, Rémi
Wilkes, Antonia
Maiti, Gourhari
Farrugia, Louis J.
Ricard, Louis
Prunet, Joëlle
Cascade Metathesis Reactions for the Synthesis of Taxane and Isotaxane Derivatives
title Cascade Metathesis Reactions for the Synthesis of Taxane and Isotaxane Derivatives
title_full Cascade Metathesis Reactions for the Synthesis of Taxane and Isotaxane Derivatives
title_fullStr Cascade Metathesis Reactions for the Synthesis of Taxane and Isotaxane Derivatives
title_full_unstemmed Cascade Metathesis Reactions for the Synthesis of Taxane and Isotaxane Derivatives
title_short Cascade Metathesis Reactions for the Synthesis of Taxane and Isotaxane Derivatives
title_sort cascade metathesis reactions for the synthesis of taxane and isotaxane derivatives
topic Full Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4982030/
https://www.ncbi.nlm.nih.gov/pubmed/27062670
http://dx.doi.org/10.1002/chem.201600592
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