Stereoselective total synthesis of (S)- and (R)-nuciferine using benzyne chemistry

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 (...

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Bibliographic Details
Published in:Tetrahedron 2020-09, Vol.76 (38), p.131461, Article 131461
Main Authors: Perecim, Givago P., Deflon, Victor M., Martins, Gabriel R., Pinto, Leandro M.C., Casagrande, Gleison A., Oliveira-Silva, Diogo, Raminelli, Cristiano
Format: Article
Language:English
Subjects:
Aporphine alkaloids
Benzyne chemistry
Chiral auxiliary
DFT calculations
Stereoselective synthesis
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Summary: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. [Display omitted] •Total syntheses of (S)- and (R)-nuciferine were accomplished through unprecedented approach involving benzyne chemistry.•Reaction between chiral dihydroisoquinoline enamide and benzyne precursor afforded a separable mixture of diastereoisomers.•The stereochemical pathway for the key transformation was evaluated by DFT calculations.•The structure of the major diastereoisomer was unequivocally confirmed by X-ray analysis.
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2020.131461