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1.
J Org Chem ; 87(2): 1325-1334, 2022 01 21.
Artigo em Inglês | MEDLINE | ID: mdl-35007075

RESUMO

An asymmetric synthetic route to (-)-galanthamine (1), a pharmacologically active Amaryllidaceae alkaloid used for the symptomatic treatment of early onset Alzheimer's disease, was successfully established with very high levels of stereocontrol. The key to achieving high chemo- and stereo-selectivity in this approach was the use of transition-metal-mediated reactions, namely, enyne ring-closing metathesis, Heck coupling, and titanium-based asymmetric allylation.


Assuntos
Alcaloides , Doença de Alzheimer , Galantamina , Humanos
2.
Org Lett ; 13(15): 3988-91, 2011 Aug 05.
Artigo em Inglês | MEDLINE | ID: mdl-21744783

RESUMO

Short routes to enantiomerically pure indolizidine and quinolizidine alkaloids have been developed using imino-aldol reactions of enolates derived from phenyl 5-chlorovalerate. High levels of syn selectivity (dr ∼13-16:1) were obtained using lithium enolates of phenyl esters in combination with tert-butylsulfinyl imines. The imino-aldol adducts were deprotected and cyclized to afford (-)-epilupinine ((-)-2) and (-)-tashiromine ((-)-1) in two further steps.


Assuntos
Aldeídos/química , Iminas/química , Indolizinas/síntese química , Esparteína/análogos & derivados , Ciclização , Estrutura Molecular , Esparteína/síntese química
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