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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Detalles Bibliográficos
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
Descripción
Sumario: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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