1. Total synthesis of putative 11-epi-lyngbouilloside aglycon
- Author
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Amandine Kolleth, Julian Gebauer, Abdellatif El Marrouni, Raphael Lebeuf, Celine Prevost, Eric Brohan, Stellios Arseniyadis, and Janine Cossy
- Subjects
Total synthesis ,RCM ,Mukaiyama aldol ,Lyngbouilloside ,Lyngya bouillonii ,Boeckman esterification ,Chemistry ,QD1-999 - 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.
- Published
- 2016
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