1206475-97-9Relevant academic research and scientific papers
Concise Asymmetric Total Synthesis of ent-Ancistrocladinium A
Kim, Kyung-Hee,Cheon, Cheol-Hong
, p. 2883 - 2888 (2016)
An asymmetric total synthesis of ent-ancistrocladinium A was developed via chiral phosphoric acid-catalyzed asymmetric reductive amination of 1-aryl-2-propanone and naphthylamine followed by a Bischler–Napieralski reaction. Direct use of the naphthyl moiety in the amine as a key building block in the natural product allowed us to achieve the total synthesis of ancistrocladinium A in only three steps from the known starting materials. (Figure presented.).
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).
