Biscarbazoles are a class of carbazole alkaloids in which two carbazole moieties are connected by different linkages. Oxydimurrayafoline is a special biscarbazole connecting two carbazole units via a benzylic ether linkage at the 3-position.
In this HOT Communication, Hans-Joachim Knölker and co-workers from Technische Universität Dresden, report the first total synthesis of oxydimurrayafoline via nucleophilic substitution at the benzylic position at the C-3 position of the carbazole framework.
Knölker et al. use a palladium catalysis approach to produce the key intermediate mukonine in 2 steps before going on to make oxydimurrayafoline in a total of 6 steps with an overall yield of 43%.
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First total synthesis of the biscarbazole alkaloid oxydimurrayafoline
Carsten Börger, Micha P. Krahl, Margit Gruner, Olga Kataeva and Hans-Joachim Knölker