100108-68-7

Upstream product

• 2835-98-5 2-Hydroxy-4-methylanilin 
• 766-85-8 3-methoxy-1-iodobenzene 
• 107672-59-3 1-acetoxy-7-hydroxy-3-methylcarbazole 
• 107672-50-4 1-hydroxy-7-methoxy-3-methylcarbazole 
• 107672-51-5 1,7-dihydroxy-3-methylcarbazole 
• 115-18-4 2-methyl-3-buten-2-ol 

Downstream Products

• 89368-92-3 bismurrayafoline-B 

Relevant academic research and scientific papers

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

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.

Synthesis of Murrayafoline-B and Murrayaquinone-B

Murrayafoline-B (1) has been synthesised starting from 7-methoxy-3-methyl-1-oxo-1,2,3,4-tetrahydrocarbazole (4) by a sequence of reactions, such as, aromatisation, demethylation, monoacetylation, prenylation followed by methylation and finally deacetylation.Pyridinium chlorochromate oxidation of murrayafoline-B affords murrayaquinone-B (2) in a moderate yield.