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Enantioselective synthesis of naturally occurring isoquinoline alkaloids: (S)-(−)-trolline and (R)-(+)-oleracein E

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Abstract

The highly efficient asymmetric syntheses of a pair of enantiomers, (S)-(−)-trolline and (R)-(+)-oleracein E, from commercially available 2-methyl-3-butyn-2-ol, benzaldehyde and 6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline have been achieved in five steps with the catalytic enantioselective C1-alkynylation of 6,7-dimethoxy-3,4-dihydroisoquinoline as a key step, providing an efficient general approach for this type of naturally occurring chiral isoquinoline alkaloids.

Graphical abstract: Enantioselective synthesis of naturally occurring isoquinoline alkaloids: (S)-(−)-trolline and (R)-(+)-oleracein E

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Publication details

The article was received on 22 Jan 2017, accepted on 04 Mar 2017 and first published on 06 Mar 2017


Article type: Research Article
DOI: 10.1039/C7QO00062F
Citation: Org. Chem. Front., 2017, Advance Article
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    Enantioselective synthesis of naturally occurring isoquinoline alkaloids: (S)-(−)-trolline and (R)-(+)-oleracein E

    W. Lin and S. Ma, Org. Chem. Front., 2017, Advance Article , DOI: 10.1039/C7QO00062F

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