1206475-90-2Relevant academic research and scientific papers
Total synthesis of the N,C-coupled naphthylisoquinoline alkaloids ancistrocladinium A and B and related analogues
Bringmann, Gerhard,Gulder, Tanja,Hertlein, Barbara,Hemberger, Yasmin,Meyer, Frank
supporting information; experimental part, p. 1151 - 1158 (2010/04/01)
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).
