Total syntheses of murrayamine E, I, and K.
We describe efficient synthetic routes to murrayamine A (mukoenine C), O-methylmurrayamine A, mahanine, O-methylmahanine, and murrayamine D and the first total syntheses of murrayamine E, I, and K. Key steps are a palladium-catalyzed construction of the carbazole framework and an annulation of the pyran ring, which is either catalyzed by phenylboronic acid or promoted by a Lewis acid.
Department Chemie, Technische Universität Dresden, Bergstrasse 66, 01069 Dresden, Germany.
Christian
C
Schuster
Department Chemie, Technische Universität Dresden, Bergstrasse 66, 01069 Dresden, Germany.
Konstanze K
KK
Julich-Gruner
Department Chemie, Technische Universität Dresden, Bergstrasse 66, 01069 Dresden, Germany.
Heinrich
H
Schnitzler
Department Chemie, Technische Universität Dresden, Bergstrasse 66, 01069 Dresden, Germany.
Ronny
R
Hesse
Department Chemie, Technische Universität Dresden, Bergstrasse 66, 01069 Dresden, Germany.
Anne
A
Jäger
Department Chemie, Technische Universität Dresden, Bergstrasse 66, 01069 Dresden, Germany.
Arndt W
AW
Schmidt
Department Chemie, Technische Universität Dresden, Bergstrasse 66, 01069 Dresden, Germany.
Hans-Joachim
HJ
Knölker
D000470:Alkaloids / Q000737:chemistry*; D002227:Carbazoles / Q000138:chemical synthesis* / Q000737:chemistry*; D002384:Catalysis; D058116:Lewis Acids / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
D000470:Alkaloids; D002227:Carbazoles; D058116:Lewis Acids; C558545:O-methylmurrayamine A; C465290:mahanine; C041514:carbazole