Synfacts 2010(5): 0552-0552  
DOI: 10.1055/s-0029-1219701
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Expedient Total Synthesis of Kinamycin F

Contributor(s): Mark Lautens, David A. Candito
C. M. Woo, L. Lu, S. L. Gholap, D. R. Smith, S. B. Herzon*
Yale University, New Haven, USA
Further Information

Publication History

Publication Date:
22 April 2010 (online)

Significance

The kinamycins are an interesting class of natural products featuring an unusual ­diazonaphthoquinone function. Their unique molecular architecture and potent biological activities have made them desirable targets for total synthesis. The group of Porco was the first to disclose a stereoselective synthesis of kinamycin C (X. Lei, J. A. Porco J. Am. Chem. Soc. 2006, 128, 14790) and later the Nicolaou group reported the syntheses of kinamycins C, F and J (K. C. Nicolaou et al. J. Am. Chem. Soc. 2007, 129, 10356). The authors report an expedient total synthesis of kinamycin F, believed to be the active in vivo form of the kinamycins. The key features of the synthesis are a convergent ring formation strategy and a diazo-transfer reaction.