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Pure Appl. Chem., 2010, Vol. 82, No. 11, pp. 1975-1991

Published online 2010-08-06

Total synthesis of biologically active alkaloids using transition metals

Ronny Forke1, Konstanze K. Gruner1, Kerstin E. Knott1, Stefan Auschill1, Sameer Agarwal1, René Martin1, Markus Böhl2, Sabine Richter2, Georgios Tsiavaliaris3, Roman Fedorov3, Dietmar J. Manstein3, Herwig O. Gutzeit2 and Hans-Joachim Knölker1*

1 Department of Chemistry, Technical University of Dresden, Bergstrasse 66, 01069 Dresden, Germany
2 Institute of Zoology, Technical University of Dresden, Zellescher Weg 20b, 01217 Dresden, Germany
3 Institute for Biophysical Chemistry, Hannover Medical School, 30623 Hannover, Germany

Abstract: We have developed efficient synthetic routes to heterocyclic ring systems using transition metals (palladium, iron, and silver). Recent applications of this chemistry to the total synthesis of biologically active alkaloids include carbazole alkaloids (pityriazole, euchrestifoline, the antiostatins), crispine A, pentabromo- and pentachloropseudilin. The two latter alkaloids represent a novel class of myosin ATPase inhibitors that led to the discovery of a new allosteric binding site of the protein.