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Synthesis 2017; 49(02): 275-292
DOI: 10.1055/s-0036-1588322
DOI: 10.1055/s-0036-1588322
paper
Palladium-Catalyzed Synthesis of Pyrayaquinones, Murrayaquinones, and Murrayafoline-B
Further Information
Publication History
Received: 08 August 2016
Accepted after revision: 06 September 2016
Publication Date:
11 October 2016 (online)
Dedicated to Professor Dieter Enders on the occasion of his 70th 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 openingSupporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0036-1588322.
- Supporting Information
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