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  • Title: Total synthesis of the N,C-coupled naphthylisoquinoline alkaloids ancistrocladinium A and B and related analogues.
    Author: Bringmann G, Gulder T, Hertlein B, Hemberger Y, Meyer F.
    Journal: J Am Chem Soc; 2010 Jan 27; 132(3):1151-8. PubMed ID: 20043699.
    Abstract:
    The N,C-coupled naphthyldihydroisoquinoline alkaloids ancistrocladinium A (3) and B (4), which possess an unprecedented iminium-aryl axis and show high in vitro antileishmanial activities, have been synthesized via a short sequence of eight linear steps, without the need of protecting groups. Key steps were a Buchwald-Hartwig amination and a Bischler-Napieralski cyclization, preferentially leading to the naturally predominant M-atropo-diastereomer in the case of 3, while the N,C-axis is configurationally semistable in 4. The highly convergent first access to this type of alkaloids will now facilitate the preparation of structural analogues for structure-activity relationship studies. Its general applicability was shown by the preparation of the sterically even more congested, as yet unnatural N,3'- and N,1'-coupled analogues, ancistrocladinium C (5) and D (6).
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