Palladium-Catalyzed Synthesis of Pyrayaquinones, Murraya­quinones, and Murrayafoline-B

Dedicated to Professor Dieter Enders on the occasion of his 70^th birthday.

Abstract

We describe the total synthesis of murrayafoline-B and seven carbazole-1,4-quinone alkaloids. A palladium(II)-catalyzed oxidative cyclization is used to construct the carbazole skeleton. Pyran annulation and oxidation provide pyrayaquinone-A, -B, and -C. DIBAL-H-promoted reductive ring opening of pyrano[3,2-a]carbazole precursors leads to the prenylated and geranylated carbazole-1,4-quinone alkaloids murrayaquinone-B, -C, -D, and -E and to murrayafoline-B.

Key words

carbazole - alkaloids - quinones - natural products - total synthesis - palladium - Frémy’s salt - ring opening

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