title: Total Synthesis of Putative 11-epi-Lyngbouilloside Aglycon.
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.
authors.affiliation: Laboratoire de Chimie Organique, Institute of Chemistry, Biology and Innovation, ESPCI Paris, Centre National de la Recherche Scientifique (UMR8231), PSL Research University Paris, France.
authors.forename: Amandine
authors.initials: A
authors.lastname: Kolleth
authors.affiliation: Laboratoire de Chimie Organique, Institute of Chemistry, Biology and Innovation, ESPCI Paris, Centre National de la Recherche Scientifique (UMR8231), PSL Research University Paris, France.
authors.forename: Julian
authors.initials: J
authors.lastname: Gebauer
authors.affiliation: Laboratoire de Chimie Organique, Institute of Chemistry, Biology and Innovation, ESPCI Paris, Centre National de la Recherche Scientifique (UMR8231), PSL Research University Paris, France.
authors.forename: Abdelatif
authors.initials: A
authors.lastname: ElMarrouni
authors.affiliation: Laboratoire de Chimie Organique, Institute of Chemistry, Biology and Innovation, ESPCI Paris, Centre National de la Recherche Scientifique (UMR8231), PSL Research University Paris, France.
authors.forename: Raphael
authors.initials: R
authors.lastname: Lebeuf
authors.affiliation: LGCR-Analytical Sciences, Sanofi Vitry-sur-Seine, France.
authors.forename: Céline
authors.initials: C
authors.lastname: Prévost
authors.affiliation: LGCR-Analytical Sciences, Sanofi Vitry-sur-Seine, France.
authors.forename: Eric
authors.initials: E
authors.lastname: Brohan
authors.affiliation: Laboratoire de Chimie Organique, Institute of Chemistry, Biology and Innovation, ESPCI Paris, Centre National de la Recherche Scientifique (UMR8231), PSL Research University Paris, France.
authors.forename: Stellios
authors.initials: S
authors.lastname: Arseniyadis
authors.affiliation: Laboratoire de Chimie Organique, Institute of Chemistry, Biology and Innovation, ESPCI Paris, Centre National de la Recherche Scientifique (UMR8231), PSL Research University Paris, France.
authors.forename: Janine
authors.initials: J
authors.lastname: Cossy
keywords: Boeckman esterification; Lyngbya bouillonii; Mukaiyama aldol; asymmetric Sharpless dihydroxylation; lyngbouilloside; ring-closing metathesis; total synthesis