A Short Synthesis of the Bacterial Pigments Violacein and Deoxyviolacein

Gregor Wille; Wolfgang Steglich

doi:10.1055/s-2001-12776

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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;

Abstract

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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

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References

1a Wrede F. Rothhaas A. Hoppe-Seyler’s Z. Physiol. Chem. 1934, 223: 113

1b Strong FM. Science 1944, 100: 287

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

4a Shirata A. Tsukamoto T. Yasui H. Kato H. Hayasaka S. Kojima A. Nippon Sanshigaku Zassh 1997, 66: 377

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

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

7 Lichstein HC. Van deSand VF. J. Bact. 1946, 52: 145

8a Haun M. Pereira MF. Hoffmann ME. Joyas A. Campos V. Filardi LDS. DeCastro SL. Durán N. Biol. Res. 1992, 25: 21

8b Durán N. Antônio RV. Haun M. Pilli RA. World J. Microbiol. Biotechnol. 1994, 10: 686

9a Hoshino T. Kondo T. Uchiyama T. Ogasawara N. Agric. Biol. Chem. 1987, 51: 965

9b Hoshino T. Kojima Y. Hayashi T. Uchiyama T. Kaneko K. Biosci. Biotechnol. Biochem. 1993, 57: 775

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

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

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

12 Nagasaka T. Abe M. Ozawa N. Kosugi Y. Hamaguchi F. Heterocycles 1983, 20: 985

13 Brenner M. Mayer G. Terpin A. Steglich W. Chem. Eur. J. 1997, 3: 70

14

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

15 Hoshino T. Ogasawara N. Agric. Biol. Chem. 1990, 54: 2339

16 Heller G. Lauth H. J. prakt. Chem. 1926, 113: 225

17a

Purchased from Aldrich Ltd., Nr. B2,780-3

17b Ohkubo M. Nishimura T. Jona H. Honma T. Morishima H. Tetrahedron 1996, 52: 8099