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Synthesis of Methylene‐Bridged Biscarbazole Alkaloids by using an Ullmann‐type Coupling: First Total Synthesis of Murrastifoline‐C and Murrafoline‐E
Author(s) -
Kutz Sebastian K.,
Börger Carsten,
Schmidt Arndt W.,
Knölker HansJoachim
Publication year - 2016
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201504680
Subject(s) - carbazole , total synthesis , methylene , palladium , ullmann reaction , chemistry , sequence (biology) , coupling (piping) , coupling reaction , stereochemistry , combinatorial chemistry , organic chemistry , materials science , catalysis , biochemistry , metallurgy
We describe the total synthesis of methylene‐bridged biscarbazole alkaloids by using a late‐stage Ullmann‐type coupling of fully functionalised carbazole subunits. The carbazole derivatives were synthesised via a sequence of palladium(0)‐ and palladium(II)‐catalysed coupling reactions. Our approach has provided bismurrayafoline‐A, bismurrayafolinol, chrestifolines B–D, and the first total synthesis of murrastifoline‐C and murrafoline‐E.