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Synfacts 2006(5): 0421-0421  
DOI: 10.1055/s-2006-934394
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Fredericamycin A

Contributor(s): Philip Kocienski, Thomas Snaddon
S. Akai, T. Tsujino, N. Fukuda, K. Iio, Y. Takeda, K. Kawaguchi, T. Naka, K. Higuchi, E. Akiyama, H. Fujioka, Y. Kita*
Osaka University, Japan
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Publikationsdatum:
21. April 2006 (online)

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Significance

Fredericamycin A is active in vivo against several tumor lines and it inhibits topo­isomerases I and II. Noteworthy in this synthesis are (1) the oxidative intramolecular [4+2] cycloaddition of (phenylthio)acetylene-cobalt complex A and (2) an interesting aromatic Pummerer-type rearrangement used to convert diaryl thioether D into the phenol ester J.