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Synfacts 2008(1): 0001-0001  
DOI: 10.1055/s-2007-991496
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Kinamycin C

Contributor(s):Philip Kocienski, Zofia Komsta
K. C. Nicolaou*, H. Li, A. L. Nold, D. Pappo, A. Lenzen
The Scripps Research Institute and University of California at San Diego, La Jolla, USA
Total Synthesis of Kinamycins C, F, and J
J. Am. Chem. Soc.  2007,  129:  10356-10357  
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Publication History

Publication Date:
18 December 2007 (online)

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Key words

Ullmann reaction - allylic oxidation - Stetter reaction

Significance

Kinamycins are Streptomyces metabolites that contain a rare diazofluorene moiety. Kinamycin C possesses strong inhibiting activity against Gram-positive bacteria along with some antitumor activity. A convergent synthesis is presented in which both key building blocks A and B can be synthesized on a multigram scale.

Comment

Addition of catalytic amounts of CuI markedly improved the yield in the Ullmann coupling of A and B. A substoichiometric amount of triazolium salt D (T. Rovis and co-workers J. Org. Chem. 2005, 70, 5725) mediated a Stetter-type trans­formation to construct the cyclopentanone ring. TBS-protected kinamycin C can be easily transformed into kinamycins F and J.

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