First total synthesis of the 7-oxygenated carbazole alkaloids clauszoline-K, 3-formyl-7-hydroxycarbazole, clausine M, clausine N and the anti-HIV active siamenol using a highly efficient palladium-catalyzed approach.
Using a convergent palladium-catalyzed construction of the carbazole framework as the key step we have achieved a short synthesis of the 7-oxygenated carbazole alkaloids clauszoline-K, 3-formyl-7-hydroxycarbazole, clausine C (clauszoline-L), clausine M, clausine N and the anti-HIV active siamenol.
Krahl
Micha P
MP
Department Chemie, Technische Universität Dresden, Bergstrasse 66, 01069 Dresden, Germany.
Jäger
Anne
A
Krause
Tilo
T
Knölker
Hans-Joachim
HJ
D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D019380:Anti-HIV Agents / Q000138:chemical synthesis* / Q000737:chemistry; D002227:Carbazoles / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D006575:Heterocyclic Compounds, 3-Ring / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D008968:Molecular Conformation; D010165:Palladium
D000470:Alkaloids; D019380:Anti-HIV Agents; D002227:Carbazoles; D006575:Heterocyclic Compounds, 3-Ring; C523057:clausine M; C523056:clausine N; C523055:clauszoline-K; D010165:Palladium