Stereoselective total synthesis of the putative structure of nitraraine

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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/2445/99223

dc.contributor	Universitat de Barcelona
dc.contributor.author	Arioli, Federica
dc.contributor.author	Pérez Bosch, Maria
dc.contributor.author	Subrizi, Fabiana
dc.contributor.author	Llor Brunés, Núria
dc.contributor.author	Bosch Cartes, Joan
dc.contributor.author	Amat Tusón, Mercedes
dc.date	2016-06-03T14:44:09Z
dc.date	2016-06-03T14:44:09Z
dc.date	2014-08-15
dc.date	2016-06-03T14:44:14Z
dc.identifier.citation	0022-3263
dc.identifier.citation	643223
dc.identifier.uri	http://hdl.handle.net/2445/99223
dc.format	6 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/jo5013543
dc.relation	Journal of Organic Chemistry, 2014, vol. 79, num. 16, p. 7740-7745
dc.relation	http://dx.doi.org/10.1021/jo5013543
dc.rights	(c) American Chemical Society , 2014
dc.rights	info:eu-repo/semantics/openAccess
dc.subject	Alcaloides
dc.subject	Síntesi orgànica
dc.subject	Lactames
dc.subject	Compostos heterocíclics
dc.subject	Triptòfan
dc.subject	Alkaloids
dc.subject	Organic synthesis
dc.subject	Lactams
dc.subject	Heterocyclic compounds
dc.subject	Tryptophan
dc.title	Stereoselective total synthesis of the putative structure of nitraraine
dc.type	info:eu-repo/semantics/article
dc.type	info:eu-repo/semantics/acceptedVersion
dc.description.abstract	After the structure originally proposed for nitraraine was shown to be incorrect by total synthesis, the alternative structure 5 was recently suggested for the alkaloid on biosynthetic grounds and by comparison with the (1)H NMR data of tangutorine. The unambiguous synthesis of 5 is reported from tryptophanol and ketodiester 6, via oxazoloquinolone lactam 7. However, the melting point and (1)H NMR data of 5 did not match those reported for the natural product.

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