Access to Enantiopure 5‑, 7‑, and 5,7-Substituted cis- Decahydroquinolines: Enantioselective Synthesis of (−)-Cermizine B

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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/2445/111625

dc.contributor	Universitat de Barcelona
dc.contributor.author	Pinto, Alexandre
dc.contributor.author	Griera Farres, Rosa
dc.contributor.author	Molins i Grau, Elies
dc.contributor.author	Fernández Cadenas, Israel
dc.contributor.author	Bosch Cartes, Joan
dc.contributor.author	Amat Tusón, Mercedes
dc.date	2017-05-26T14:08:21Z
dc.date	2017-03-21
dc.date	2017-05-26T14:08:22Z
dc.date	info:eu-repo/date/embargoEnd/2018-03-21
dc.identifier.citation	1523-7060
dc.identifier.citation	671054
dc.identifier.uri	http://hdl.handle.net/2445/111625
dc.format	4 p.
dc.format	application/pdf
dc.language.iso	eng
dc.publisher	American Chemical Society
dc.relation	Versió postprint del document publicat a: https://doi.org/10.1021/acs.orglett.7b00492
dc.relation	Organic Letters, 2017, vol. 19, p. 1714-1717
dc.relation	https://doi.org/10.1021/acs.orglett.7b00492
dc.rights	(c) American Chemical Society , 2017
dc.rights	info:eu-repo/semantics/embargoedAccess
dc.subject	Alcaloides
dc.subject	Lactames
dc.subject	Alkaloids
dc.subject	Lactams
dc.title	Access to Enantiopure 5‑, 7‑, and 5,7-Substituted cis- Decahydroquinolines: Enantioselective Synthesis of (−)-Cermizine B
dc.type	info:eu-repo/semantics/article
dc.type	info:eu-repo/semantics/acceptedVersion
dc.description.abstract	Stereoconvergent cyclocondensation reactions of (R)- or (S)-phenylglycinol with appropriately substituted cyclohexanone-based δ-keto esters are the key steps of short synthetic routes to enantiopure 5-, 7-, and 5,7-substituted cisdecahydroquinolines. The factors governing the stereoselectivity of the cyclocondensation are discussed. The potential of the methodology is illustrated by a protecting-group-free synthesis of the phlegmarine-type Lycopodium alkaloid (-)-cermizine B.

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