Total Synthesis of Hydroazulene Natural Products
Dr. Peter Metz
Department of Chemistry and Food Chemistry
Monday, August 18, 2014
C2 361 (Reading Room)
Abstract: The bicyclo[5.3.0]decane (hydroazulene) ring system is present in many natural products. A metathesis approach provided rapid access to the guaiane sesquiterpene (-)-englerin A (1) that shows a potent and highly selective action against renal cancer cell lines.1 Ongoing work towards several other guaianes will be discussed as well.2
The diterpene kempene-2 (2) incorporates the hydroazulene moiety as part of the complex tetracyclic kempane framework. A domino metathesis was the key step in the first enantioselective total synthesis of this kempane and structurally related compounds isolated from the soldier defense secretion of higher termites.2
1 M. Zahel, A. Keßberg, P. Metz, Angew. Chem. 2013, 125, 5500-5502; Angew. Chem. Int. Ed. 2013, 52, 5390-5392.
2 M. Zahel, P. Metz, Beilstein J. Org. Chem. 2013, 9, 2028-2032.
2 M. Schubert, P. Metz, Angew. Chem. 2011, 123, 3011-3013; Angew. Chem. Int. Ed. 2011, 50, 2954-2956.