Download PDF
Synthesis 2010(12): 2023-2026  
DOI: 10.1055/s-0029-1218744
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of a Cyclopent[g]isoquinoline Building Block for Fredericamycin A

Manfred Braun*a, Gwenaëlle Kergoëta, Fabian Kruskaa, Walter Frankb
a Institut für Organische Chemie und Makromolekulare Chemie, Universität Düsseldorf, 40225 Düsseldorf, Germany
Fax: +49(211)8115079; e-Mail: braunm@uni-duesseldorf.de;
b Institut für Anorganische Chemie und Strukturchemie, Universität Düsseldorf, 40225 Düsseldorf, Germany
Further Information

Publication History

Received 6 January 2010
Publication Date:
15 April 2010 (online)

   Permissions and Reprints All articles of this category
Preview

Abstract

A new route to the DEF-ring building block of fredericamycin A has been elaborated. The five-step synthesis involves a photo-Wolff reaction as the key step and leads to carboxylic acid 2 in 27% overall yield, starting from the pyridine derivative 3. Two intermediates, the tricyclic ketones 6a and 7, are characterized by crystal structure analyses.

Key words

heterocycles - rearrangement - diazo compounds - annulation - carboxylic acids

    References

  • 1a Pandey RC. Toussaint MW. Stroshane RM. Kalita CC. Aszalos AA. Garretson AL. Wei TT. Byrne KM. Geoghegan RF. White RJ. J. Antibiot.  1981,  34:  1389 
    Search in Google Scholar
  • 1b Misra R. Pandey RC. Silverton JV. J. Am. Chem. Soc.  1982,  104:  4478 
    Search in Google Scholar
  • 1c Misra R. Pandey RC. Hilton BD. Roller PP. Silverton JV. J. Antibiot.  1987,  40:  786 
    Search in Google Scholar
  • 1d Chen Y. Wendt-Pienkowski E. Shen B. J. Bacteriol.  2008,  190:  5587 
    Search in Google Scholar
  • 1e Wendt-Pienkowski E. Huang Y. Zhang J. Li B. Jiang H. Kwon H. Hutchinson CR. Shen B. J. Am. Chem. Soc.  2005,  127:  16442 
    Search in Google Scholar
  • 2a Warnick-Pickle DJ. Byrne KM. Pandey RC. White RJ. J. Antibiot.  1981,  34:  1402 
    Search in Google Scholar
  • 2b Misra R. J. Antibiot.  1988,  41:  976 
    Search in Google Scholar
  • 2c Latham MD. King CK. Gorycki P. Macdonald TL. Ross WE. Cancer Chemother. Pharmacol.  1989,  24:  167 
    Search in Google Scholar
  • 2d Dalal NS. Shi X. Biochemistry  1989,  28:  748 
    Search in Google Scholar
  • 3 Abel U. Simon W. Eckard P. Hansske FG. Bioorg. Med. Chem. Lett.  2006,  16:  3292 
    CrossrefSearch in Google Scholar
  • 4a Kelly TR. Bell SH. Ohashi N. Armstrong-Chong RJ. J. Am. Chem. Soc.  1988,  110:  6471 
    Search in Google Scholar
  • 4b Clive DLJ. Tao Y. Khodabocus A. Wu Y.-J. Angoh AG. Bennett SM. Boddy CN. Bordeleau L. Kellner D. Kleiner G. Middleton DS. Nichols CJ. Richardson SR. Vernon PG. J. Am. Chem. Soc.  1994,  116:  11275 
    Search in Google Scholar
  • 4c Rao AVR. Singh AK. Rao BV. Reddy KM. Heterocycles  1994,  37:  1893 
    Search in Google Scholar
  • 4d Saint-Jalmes L. Lila C. Xu JZ. Moreau L. Pfeiffer B. Eck G. Pelsez L. Rolando C. Julia M. Bull. Soc. Chim. Fr.  1993,  130:  447 
    Search in Google Scholar
  • 4e Wendt JA. Gauvreau PJ. Bach RD. J. Am. Chem. Soc.  1994,  116:  9921 
    Search in Google Scholar
  • 4f Kita Y. Iio K. Kawaguchi K. Fukuda N. Takeda Y. Ueno H. Okunaka R. Higuchi K. Tsujino T. Fujioka H. Akai S. Chem. Eur. J.  2000,  6:  3897 
    Search in Google Scholar
  • 5 Boger DL. Hüter O. Mbiya K. Zhang M. J. Am. Chem. Soc.  1995,  117:  11839 
    Search in Google Scholar
  • 6 Akai S. Tsujino T. Fukuda N. Iio K. Takeda Y. Kawaguchi K. Naka T. Higuchi K. Akiyama E. Fujioka H. Kita Y. Chem. Eur. J.  2005,  11:  6286 
    CrossrefSearch in Google Scholar
  • 7 Clive DLJ. Sedgeworth J. J. Heterocycl. Chem.  1987,  24:  509 
    CrossrefSearch in Google Scholar
  • 8 For a review, see: Snieckus V. Chem. Rev.  1990,  90:  879 
    Search in Google Scholar
  • 9 Lombardo L. Mander LN. Synthesis  1980,  368 
    Thieme Connect
  • 10 For a review, see: Kirmse W. Eur. J. Org. Chem.  2002,  2193 
    Crossref
  • 11 Sheldrick GM. SHELXS86. Program for the Solution of Crystal Structures   University of Göttingen; Germany: 1985. 
  • 12 Sheldrick GM. SHELXL97. Program for the Refinement of Crystal Structures   University of Göttingen; Germany: 1997. 
13

Crystallographic data (excluding structure factors) for the structures reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC 758035 (6a) and CCDC 758036 (7). Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [fax: +44(1223)336033 or e-mail: deposit@ccdc.cam.ac.uk].