AUTHOR=Kolleth Amandine , Gebauer Julian , ElMarrouni Abdelatif , Lebeuf Raphael , Prévost Céline , Brohan Eric , Arseniyadis Stellios , Cossy Janine 

TITLE=Total Synthesis of Putative 11-epi-Lyngbouilloside Aglycon

JOURNAL=Frontiers in Chemistry

VOLUME=4

YEAR=2016

URL=https://www.frontiersin.org/journals/chemistry/articles/10.3389/fchem.2016.00034

DOI=10.3389/fchem.2016.00034

ISSN=2296-2646

ABSTRACT=<p>We report here the total synthesis of 11-<italic>epi</italic>-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.</p>