Download PDF
Synthesis 2001(5): 759-762
DOI: 10.1055/s-2001-12776
PAPER
© Georg Thieme Verlag Stuttgart · New York

A Short Synthesis of the Bacterial Pigments Violacein and Deoxyviolacein

Gregor Wille, Wolfgang Steglich*
Department Chemie, Ludwig-Maximilians-Universität München, Butenandtstr. 5-13, 81377 München, Germany
Fax: +49(89)21807756; e-Mail: wos@cup.uni-muenchen.de;
Further Information

Publication History

Received 30 January 2001
Publication Date:
15 October 2004 (online)

    Permissions and Reprints All articles of this category

Abstract

A concise synthesis of the bacterial pigments deoxyviolacein (1a) and violacein (1b) is described in which two indole units are attached stepwise to the central pyrrolinone ring.

Key words

total synthesis - natural products - bacterial pigments - violacein - indoles

    References

  • 1a Wrede F. Rothhaas A. Hoppe-Seyler’s Z. Physiol. Chem.  1934,  223:  113 
    Search in Google Scholar
  • 1b Strong FM. Science  1944,  100:  287 
    Search in Google Scholar
  • 1c Beer RJS. Clarke K. Khorana HG. Robertson A. J. Chem. Soc.  1949,  885 , and references cited therein
  • 2 Ballantine JA. Barrett CB. Beer RJS. Eardley S. Robertson A. Shaw BL. Simpson TH. J. Chem. Soc.  1958,  755 
  • 3 Laatsch H. Thomson RH. Cox PJ. J. Chem. Soc., Perkin Trans. 2  1984,  1331 
    Crossref
  • 4a Shirata A. Tsukamoto T. Yasui H. Kato H. Hayasaka S. Kojima A. Nippon Sanshigaku Zassh  1997,  66:  377 
    Search in Google Scholar
  • 5 DeAzevedo MBM. Alderete J. Rodriguez JA. Souza AO. Rettori D. Torsoni MA. Faljoni-Alario A. Haun M. Durán N. J. Inclusion Phenom. Macrocyclic Chem.  2000,  37:  93 
    CrossrefSearch in Google Scholar
  • 6a Hoshino T. Kojima Y. Takano T. Uchiyama T. In Frontiers and New Horizons in Amino Acid Research   Takai K. Elsevier; Amsterdam: 1992.  p.p 379 
  • 6b DaSilva Melo Silvya Stuchi Maria P. DeCampos Vidal B. Haun M. Durán N. In Vitro Cell. Dev. Biol.  2000,  36:  539 
    Search in Google Scholar
  • 7 Lichstein HC. Van deSand VF. J. Bact.  1946,  52:  145 
    Search in Google Scholar
  • 8a Haun M. Pereira MF. Hoffmann ME. Joyas A. Campos V. Filardi LDS. DeCastro SL. Durán N. Biol. Res.  1992,  25:  21 
    Search in Google Scholar
  • 8b Durán N. Antônio RV. Haun M. Pilli RA. World J. Microbiol. Biotechnol.  1994,  10:  686 
    Search in Google Scholar
  • 9a Hoshino T. Kondo T. Uchiyama T. Ogasawara N. Agric. Biol. Chem.  1987,  51:  965 
    Search in Google Scholar
  • 9b Hoshino T. Kojima Y. Hayashi T. Uchiyama T. Kaneko K. Biosci. Biotechnol. Biochem.  1993,  57:  775 
    Search in Google Scholar
  • 9c Hoshino T. Hayashi T. Odajima T. J. Chem. Soc., Perkin Trans. 1  1995,  1565 
  • 9d Ruhul Momen AZM. Hoshino T. Biosci. Biotechnol. Biochem.  2000,  64:  539 
    Search in Google Scholar
  • 9e August PR. Grossman TH. Minor C. Draper MP. MacNeil IA. Pemberton JM. Call KM. Holt D. Osburne MS. J. Mol. Microbiol. Biotechnol.  2000,  2:  513 
    Search in Google Scholar
  • 10 Ballantine JA. Beer RJS. Crutchley DJ. Dodd GM. Palmer DR. J. Chem. Soc.  1960,  2292 
  • 11 Bocchi V. Gardini GP. Org. Prep. Proced. Int.  1969,  1:  271 
    Search in Google Scholar
  • 12 Nagasaka T. Abe M. Ozawa N. Kosugi Y. Hamaguchi F. Heterocycles  1983,  20:  985 
    CrossrefSearch in Google Scholar
  • 13 Brenner M. Mayer G. Terpin A. Steglich W. Chem. Eur. J.  1997,  3:  70 
    CrossrefSearch in Google Scholar
  • 15 Hoshino T. Ogasawara N. Agric. Biol. Chem.  1990,  54:  2339 
    Search in Google Scholar
  • 16 Heller G. Lauth H. J. prakt. Chem.  1926,  113:  225 
    Search in Google Scholar
  • 17a

    Purchased from Aldrich Ltd., Nr. B2,780-3
    Crossref
  • 17b Ohkubo M. Nishimura T. Jona H. Honma T. Morishima H. Tetrahedron  1996,  52:  8099 
    CrossrefSearch in Google Scholar
14

LiHMDS appeared to be superior to LDA or LDA/TMSCl in the aldol reaction of 6a/b with 7