Total Synthesis of Putative 11-epi-Lyngbouilloside Aglycon

We report here the total synthesis of 11-epi-lyngbouilloside aglycon. Our strategy features a Boeckman-type esterification followed by a RCM to form the 14-membered ring macrolactone and a late-stage side chain introduction via a Wittig olefination. Overall, the final product was obtained in 20 step...

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Autores principales: Kolleth, Amandine, Gebauer, Julian, ElMarrouni, Abdelatif, Lebeuf, Raphael, Prévost, Céline, Brohan, Eric, Arseniyadis, Stellios, Cossy, Janine
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Frontiers Media S.A. 2016
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4977289/
https://www.ncbi.nlm.nih.gov/pubmed/27556024
http://dx.doi.org/10.3389/fchem.2016.00034
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author Kolleth, Amandine
Gebauer, Julian
ElMarrouni, Abdelatif
Lebeuf, Raphael
Prévost, Céline
Brohan, Eric
Arseniyadis, Stellios
Cossy, Janine
author_facet Kolleth, Amandine
Gebauer, Julian
ElMarrouni, Abdelatif
Lebeuf, Raphael
Prévost, Céline
Brohan, Eric
Arseniyadis, Stellios
Cossy, Janine
author_sort Kolleth, Amandine
collection PubMed
description We report here the total synthesis of 11-epi-lyngbouilloside aglycon. Our strategy features a Boeckman-type esterification followed by a RCM to form the 14-membered ring macrolactone and a late-stage side chain introduction via a Wittig olefination. Overall, the final product was obtained in 20 steps and 2% overall yield starting from commercially available 3-methyl-but-3-enol. Most importantly, the strategy employed is versatile enough to eventually allow us to complete the synthesis of the natural product and irrevocably confirm its structure.
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spelling pubmed-49772892016-08-23 Total Synthesis of Putative 11-epi-Lyngbouilloside Aglycon Kolleth, Amandine Gebauer, Julian ElMarrouni, Abdelatif Lebeuf, Raphael Prévost, Céline Brohan, Eric Arseniyadis, Stellios Cossy, Janine Front Chem Chemistry We report here the total synthesis of 11-epi-lyngbouilloside aglycon. Our strategy features a Boeckman-type esterification followed by a RCM to form the 14-membered ring macrolactone and a late-stage side chain introduction via a Wittig olefination. Overall, the final product was obtained in 20 steps and 2% overall yield starting from commercially available 3-methyl-but-3-enol. Most importantly, the strategy employed is versatile enough to eventually allow us to complete the synthesis of the natural product and irrevocably confirm its structure. Frontiers Media S.A. 2016-08-09 /pmc/articles/PMC4977289/ /pubmed/27556024 http://dx.doi.org/10.3389/fchem.2016.00034 Text en Copyright © 2016 Kolleth, Gebauer, ElMarrouni, Lebeuf, Prévost, Brohan, Arseniyadis and Cossy. http://creativecommons.org/licenses/by/4.0/ This is an open-access article distributed under the terms of the Creative Commons Attribution License (CC BY). The use, distribution or reproduction in other forums is permitted, provided the original author(s) or licensor are credited and that the original publication in this journal is cited, in accordance with accepted academic practice. No use, distribution or reproduction is permitted which does not comply with these terms.
spellingShingle Chemistry
Kolleth, Amandine
Gebauer, Julian
ElMarrouni, Abdelatif
Lebeuf, Raphael
Prévost, Céline
Brohan, Eric
Arseniyadis, Stellios
Cossy, Janine
Total Synthesis of Putative 11-epi-Lyngbouilloside Aglycon
title Total Synthesis of Putative 11-epi-Lyngbouilloside Aglycon
title_full Total Synthesis of Putative 11-epi-Lyngbouilloside Aglycon
title_fullStr Total Synthesis of Putative 11-epi-Lyngbouilloside Aglycon
title_full_unstemmed Total Synthesis of Putative 11-epi-Lyngbouilloside Aglycon
title_short Total Synthesis of Putative 11-epi-Lyngbouilloside Aglycon
title_sort total synthesis of putative 11-epi-lyngbouilloside aglycon
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4977289/
https://www.ncbi.nlm.nih.gov/pubmed/27556024
http://dx.doi.org/10.3389/fchem.2016.00034
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