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Total Synthesis of Putative 11-epi-Lyngbouilloside Aglycon
Amandine Kolleth1, Julian Gebauer1, Abdelatif ElMarrouni1
1Laboratoire de Chimie Organique, Institute of Chemistry, Biology and Innovation, ESPCI Paris, Centre National de la Recherche Scientifique (UMR8231), PSL Research University Paris, France.
Abstract:
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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