Enantioselective synthesis of lepadins A D from a phenylglycinol-derived hydroquinolone lactam

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RECERCAT Home > Universitat de Barcelona > Farmacologia, Toxicologia i Química Terapèutica > Articles publicats en revistes (Farmacologia, Toxicologia i Química Terapèutica) > View document

To access the full text documents, please follow this link: http://hdl.handle.net/2445/108026

dc.contributor	Universitat de Barcelona
dc.contributor.author	Amat Tusón, Mercedes
dc.contributor.author	Pinto, Alexandre
dc.contributor.author	Griera Farres, Rosa
dc.contributor.author	Bosch Cartes, Joan
dc.date	2017-03-07T13:11:15Z
dc.date	2017-03-07T13:11:15Z
dc.date	2015-07-21
dc.date	2017-03-07T13:11:15Z
dc.identifier.citation	0947-6539
dc.identifier.citation	655588
dc.identifier.uri	http://hdl.handle.net/2445/108026
dc.format	5 p.
dc.format	application/pdf
dc.language.iso	eng
dc.publisher	Wiley-VCH
dc.relation	Versió postprint del document publicat a: https://doi.org/10.1002/chem.201501909
dc.relation	Chemistry-A European Journal, 2015, vol. 21, num. 36, p. 12804-12808
dc.relation	https://doi.org/10.1002/chem.201501909
dc.rights	(c) Wiley-VCH, 2015
dc.rights	info:eu-repo/semantics/openAccess
dc.subject	Alcaloides
dc.subject	Lactames
dc.subject	Compostos heterocíclics
dc.subject	Síntesi asimètrica
dc.subject	Alkaloids
dc.subject	Lactams
dc.subject	Heterocyclic compounds
dc.subject	Asymmetric synthesis
dc.title	Enantioselective synthesis of lepadins A D from a phenylglycinol-derived hydroquinolone lactam
dc.type	info:eu-repo/semantics/article
dc.type	info:eu-repo/semantics/acceptedVersion
dc.description.abstract	The marine alkaloids (-)-lepadins A-C and (+)-lepadin D, belonging to two diastereoisomeric series, were synthesized from an (R)-phenylglycinol-derived tricyclic lactam via a common cis-decahydroquinoline intermediate. Crucial aspects of the synthesis are the stereochemical control in the assembly of the cis-decahydroquinoline platform, in the introduction of the C2 methyl and C3 hydroxy substituents, and in the generation of the C5 stereocenter.

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