Access to enantiopure 4-substituted 1,5-aminoalcohols from phenylglycinol-derived δ-lactams: synthesis of Haliclona alkaloiods

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RECERCAT Home > Universitat de Barcelona > Institut de Biomedicina (IBUB) > Articles publicats en revistes (Institut de Biomedicina (IBUB)) > View document

To access the full text documents, please follow this link: http://hdl.handle.net/2445/99053

dc.contributor	Universitat de Barcelona
dc.contributor.author	Amat Tusón, Mercedes
dc.contributor.author	Guignard, Guillaume
dc.contributor.author	Llor Brunés, Núria
dc.contributor.author	Bosch Cartes, Joan
dc.date	2016-05-30T17:39:01Z
dc.date	2016-05-30T17:39:01Z
dc.date	2014-03-21
dc.date	2016-05-30T17:39:06Z
dc.identifier.citation	0022-3263
dc.identifier.citation	643221
dc.identifier.uri	http://hdl.handle.net/2445/99053
dc.format	11 p.
dc.format	application/pdf
dc.language.iso	eng
dc.publisher	American Chemical Society
dc.relation	Versió postprint del document publicat a: http://dx.doi.org/10.1021/jo5002627
dc.relation	Journal of Organic Chemistry, 2014, vol. 79, num. 6, p. 2792-2802
dc.relation	http://dx.doi.org/10.1021/jo5002627
dc.rights	(c) American Chemical Society , 2014
dc.rights	info:eu-repo/semantics/openAccess
dc.subject	Síntesi orgànica
dc.subject	Alcaloides
dc.subject	Lactames
dc.subject	Compostos heterocíclics
dc.subject	Organic synthesis
dc.subject	Alkaloids
dc.subject	Lactams
dc.subject	Heterocyclic compounds
dc.title	Access to enantiopure 4-substituted 1,5-aminoalcohols from phenylglycinol-derived δ-lactams: synthesis of Haliclona alkaloiods
dc.type	info:eu-repo/semantics/article
dc.type	info:eu-repo/semantics/acceptedVersion
dc.description.abstract	LiNH2BH3-promoted reductive opening of 8-substituted phenylglycinol-derived oxazolopiperidone lactams leads to enantiopure 4-substituted-5-aminopentanols, which are used as starting building blocks in the synthesis of the Haliclona alkaloids haliclorensin C, haliclorensin, and halitulin (formal). The starting lactams are easily accessible by a cyclocondensation reaction of (R)-phenylglycinol with racemic γ-subtituted δ-oxoesters, in a process that involves a dynamic kinetic resolution.

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