Total synthesis of putative 11-epi-lyngbouilloside aglycon

Autor:	Amandine Kolleth, Julian Gebauer, Abdellatif El Marrouni, Raphael Lebeuf, Celine Prevost, Eric Brohan, Stellios Arseniyadis, Janine Cossy
Jazyk:	angličtina
Rok vydání:	2016
Předmět:	Total synthesis RCM Mukaiyama aldol Lyngbouilloside Lyngya bouillonii Boeckman esterification Chemistry QD1-999
Zdroj:	Frontiers in Chemistry, Vol 4 (2016)
Druh dokumentu:	article
ISSN:	2296-2646 88945715
DOI:	10.3389/fchem.2016.00034
Popis:	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.
Databáze:	Directory of Open Access Journals
Externí odkaz:	https://doaj.org/article/6d5934a1eda343d1835af889457154d7 Zobrazit plný text záznamu View record in DOAJ