Total Synthesis of Putative 11-epi-Lyngbouilloside Aglycon

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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Main Authors: Kolleth, Amandine, Gebauer, Julian, ElMarrouni, Abdelatif, Lebeuf, Raphael, Prévost, Céline, Brohan, Eric, Arseniyadis, Stellios, Cossy, Janine
Format: Online
Language:English
Published: Frontiers Media S.A. 2016
Online Access:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4977289/
id pubmed-4977289
recordtype oai_dc
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 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.
repository_type Open Access Journal
institution_category Foreign Institution
institution US National Center for Biotechnology Information
building NCBI PubMed
collection Online Access
language English
format Online
author Kolleth, Amandine
Gebauer, Julian
ElMarrouni, Abdelatif
Lebeuf, Raphael
Prévost, Céline
Brohan, Eric
Arseniyadis, Stellios
Cossy, Janine
spellingShingle Kolleth, Amandine
Gebauer, Julian
ElMarrouni, Abdelatif
Lebeuf, Raphael
Prévost, Céline
Brohan, Eric
Arseniyadis, Stellios
Cossy, Janine
Total Synthesis of Putative 11-epi-Lyngbouilloside Aglycon
author_facet Kolleth, Amandine
Gebauer, Julian
ElMarrouni, Abdelatif
Lebeuf, Raphael
Prévost, Céline
Brohan, Eric
Arseniyadis, Stellios
Cossy, Janine
author_sort Kolleth, Amandine
title Total Synthesis of Putative 11-epi-Lyngbouilloside Aglycon
title_short 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_sort total synthesis of putative 11-epi-lyngbouilloside aglycon
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.
publisher Frontiers Media S.A.
publishDate 2016
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4977289/
_version_ 1613623583731351552

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