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DOI: 10.1055/s-2007-991496
Synthesis of Kinamycin C
Rezensent(en):Philip Kocienski, Zofia KomstaThe 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
Publikationsverlauf
Publikationsdatum:
18. Dezember 2007 (online)
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.