Synthesis, volume 49, issue 02, pages 275-292
Palladium-Catalyzed Synthesis of Pyrayaquinones, Murrayaquinones, and Murrayafoline-B
Hans-Joachim Knölker
1
,
Sebastian Kutz
1
,
H.-J. Knölker
1
Publication type: Journal Article
Publication date: 2016-10-11
Catalysis
Organic Chemistry
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.
Found
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