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Using the palladium(II)-catalyzed oxidative cyclization of a diarylamine and the annulation of a dimethylpyran ring by Lewis acid promoted reaction with prenal as key steps, the total syntheses of the 6-oxygenated pyrano[3,2-a]carbazole alkaloids koenine and koenimbine, and of the 6,7-dioxygenated pyrano[3,2-a]carbazole alkaloids koenigine and koenigicine (koenimbidine, koenidine) were achieved. Moreover, these studies led to an improved synthetic route to the 2,6-dioxygenated carbazole alkaloid glycozolidol. Mukonicine, originally published as 6,8-dimethoxypyrano[3,2-a]carbazole, was found to be identical with koenigicine. [ABSTRACT FROM AUTHOR]

Using a palladium(II)-catalyzed oxidative cyclization of an N,N-diarylamine, we have achieved the total synthesis of the 2,8-dioxygenated carbazole alkaloids carbalexin B, clausine A, clauszoline M, and 2,8-dihydroxy-3-methylcarbazole. [ABSTRACT FROM AUTHOR]