Total synthesis of biologically active alkaloids using transition metals

Forke, Ronny; Gruner, Konstanze K.; Knott, Kerstin E.; Auschill, Stefan; Agarwal, Sameer; Martin, René; Böhl, Markus; Richter, Sabine; Tsiavaliaris, Georgios; Fedorov, Roman; Manstein, Dietmar J.; Gutzeit, Herwig O.; Knölker, Hans-Joachim

doi:10.1351/PAC-CON-09-12-15

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

http://dx.doi.org/10.1351/PAC-CON-09-12-15

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.