4846-19-9Relevant articles and documents
Stereoselective total synthesis of (S)- and (R)-nuciferine using benzyne chemistry
Casagrande, Gleison A.,Deflon, Victor M.,Martins, Gabriel R.,Oliveira-Silva, Diogo,Perecim, Givago P.,Pinto, Leandro M. C.,Raminelli, Cristiano
, (2020/08/13)
Total syntheses of (S)- and (R)-nuciferine were accomplished through approach involving diastereoselective reaction between a chiral dihydroisoquinoline enamide and 2-(trimethylsilyl)phenyl trifluoromethanesulfonate promoted by CsF, affording a separable mixture of diastereoisomers, which provided (S)- and (R)-nuciferine via simple and efficient transformations.
Aporphine alkaloid synthesis and diversification via direct arylation
Lafrance, Marc,Blaquiere, Nicole,Fagnou, Keith
, p. 811 - 825 (2008/02/12)
Palladium-catalyzed direct arylation of aryl chlorides, bromides and iodides has been applied to the preparation of new aporphine analogues including C2-substituted aporphines by reaction with benzodioxole, pyridine N-oxide and pyrazine N-oxide. Successful application of direct arylation in these diversification reactions highlights its utility not only in convergent, but also in divergent synthesis. We also describe enantioselective syntheses of (R)-nornuciferine and (R)-nuciferine employing a catalytic asymmetric transfer hydrogenation in high yield and excellent enantiomeric excess. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.
