Concise Total Synthesis of Lundurines A−C Enabled by Gold Catalysis and a Homodienyl Retro-Ene/Ene Isomerization

doi:10.1021/jacs.6b01428

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RECERCAT Home > Centres de Recerca de Catalunya (CERCA) > Institut Català d'Investigació Química (ICIQ) > Papers > View document

Use this identifier to quote or link this document: http://hdl.handle.net/2072/326397

dc.contributor.author	Echavarren, Antonio M.
dc.contributor.author	Dorel, Ruth
dc.contributor.author	Muratore, Michael E.
dc.contributor.author	Kirillova, Mariia S.
dc.date.accessioned	2018-06-15T11:41:03Z
dc.date.available	2018-06-15T11:41:03Z
dc.date.issued	2016-03-10
dc.identifier.uri	http://hdl.handle.net/2072/326397
dc.format.extent	3671 p.
dc.language.iso	eng
dc.publisher	J. Am. Chem. Soc.
dc.rights	L'accés als continguts d'aquest document queda condicionat a l'acceptació de les condicions d'ús establertes per la següent llicència Creative Commons: http://creativecommons.org/licenses/by-nc-nd/4.0/
dc.source	RECERCAT (Dipòsit de la Recerca de Catalunya)
dc.subject.other	Quimica
dc.title	Concise Total Synthesis of Lundurines A−C Enabled by Gold Catalysis and a Homodienyl Retro-Ene/Ene Isomerization
dc.type	info:eu-repo/semantics/article
dc.type	info:eu-repo/semantics/draft
dc.embargo.terms	cap
dc.identifier.doi	10.1021/jacs.6b01428
dc.rights.accessLevel	info:eu-repo/semantics/openAccess
dc.description.abstract	The total synthesis of lundurines A–C has been accomplished in racemic and enantiopure forms in 11–13 and 12–14 steps, respectively, without protection/deprotection of functional groups, by a novel tandem double condensation/Claisen rearrangement, a gold(I)-catalyzed alkyne hydroarylation, a cyclopropanation via formal [3 + 2] cycloaddition/nitrogen extrusion, and a remarkable olefin migration through a vinylcyclopropane retro-ene/ene reaction that streamlines the endgame.

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