Synfacts 2009(7): 0703-0703  
DOI: 10.1055/s-0029-1217242
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Nakiterpiosin

Contributor(s):Philip Kocienski
S. Gao, Q. Wang, C. Chen*
The University of Texas Southwestern Medical Center at Dallas, USA
Synthesis and Structure Revision of Nakiterpiosin
J. Am. Chem. Soc.  2009,  131:  1410-1412  
Further Information

Publication History

Publication Date:
22 June 2009 (online)


The synthesis of nakiterpiosin, a cytotoxic sponge metabolite, features a Pd-­catalyzed carbonylative cross-coupling (KL) followed by a photo-Nazarov cyclization (LM) to create the indanone moiety.


The photo-Nazarov cyclization entails a thermal electrocyclization induced by photo­isomerization of the enone L. Lewis acid cataly-zed variants were too harsh. CuCl and DMSO ­dramatically enhanced the rate of the cross-­coupling KL.