Synthesis of Orthogonally Protected Pyrrole Tricarboxylic Acid Derivatives: Versatile Building Blocks for Pyrrole-Containing Compounds

Carsten Schmuck; Daniel Rupprecht; Christian Urban; Nicholas Walden

doi:10.1055/s-2005-918435

PAPER

Synthesis of Orthogonally Protected Pyrrole Tricarboxylic Acid Derivatives: Versatile Building Blocks for Pyrrole-Containing Compounds

Carsten Schmuck*, Daniel Rupprecht, Christian Urban, Nicholas Walden
University of Würzburg, Institute of Organic Chemistry, Am Hubland, 97074 Würzburg, Germany
Fax: +49(931)8884625; e-Mail: schmuck@chemie.uni-wuerzburg.de;

Abstract

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Abstract

The large-scale synthesis of three new orthogonally protected pyrrole tricarboxylates 1-3 is described. Using different cleavage conditions, each of the three carboxylates can be set free selectively without affecting the others, making these pyrrole derivatives versatile synthetic building blocks for a wide range of applications in natural product or supramolecular chemistry.

Key words

pyrroles - carboxylic acids - protecting groups - transesterifications - oxidations

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References

1a Vogel E. Michels M. Zander L. Lex J. Tuzun NS. Houk KN. Angew. Chem. 2003, 115: 2964

1b Sessler JL. Salvatore C. Gale PA. Coord. Chem. Rev. 2003, 240: 17

1c Katritzky AR. Rees CW. Scriven EFV. In Comprehensive Heterocyclic Chemistry Vol. 2: Pergamon; Oxford: 1996. p.1

1d Gale PA. Camiolo S. Tizzard GJ. Chapman CP. Light ME. Coles SJ. Hursthouse MB. J. Org. Chem. 2001, 66: 7849

1e Hoffmann H. Lindel T. Synthesis 2003, 1753

1f Guernion NJL. Hayes W. Curr. Org. Chem. 2004, 8: 637

2a Schmuck C. Schwegmann M. J. Am. Chem. Soc. 2005, 127: 3373

2b Schmuck C. Geiger L. J. Am. Chem. Soc. 2004, 126: 8898

2c Schmuck C. Bickert V. Org. Lett. 2003, 5: 4579

2d Schmuck C. Geiger L. Curr. Org. Chem. 2003, 7: 1485

2e Schmuck C. Chem. Eur. J. 2000, 6: 709

3a Schmuck C. Wienand W. J. Am. Chem. Soc. 2003, 125: 452

3b Schmuck C. Eur. J. Org. Chem. 1999, 2397

4 Franck B. Wegner C. Bringmann G. Fels G. Liebigs Ann. Chem. 1980, 253

5 To the best of our knowledge, in the literature only one similar system, the pyrrole derivative 16 is reported. But no detailed synthetic procedure is available: Jackson AH. Supphayen D. J. Chem. Soc., Perkin Trans. 1 1987, 277

6 Greene TW. Wuts PGM. Protective Groups in Organic Synthesis 3rd ed.: Wiley; New York: 1991.

7a Paine JB. Dolphin D. J. Org. Chem. 1985, 50: 5598

7b Lim BB. Hosmane RS. J. Org. Chem. 1985, 50: 5111

8a Shrout DP. Lightner DA. Synthesis 1990, 1062

8b Xie M. Lightner DA. Tetrahedron 1993, 49: 2185

9 Bullock E. Johnson AW. Markham E. Shaw KB. J. Chem. Soc. 1958, 1430

10a Holmes DL. Lightner DA. Tetrahedron 1995, 51: 1607

10b Dörner T. Knipp B. Lightner DA. Tetrahedron 1997, 53: 2697

10c Boiadjiev SE. Lightner DA. Tetrahedron: Asymmetry 1997, 21: 3503

11 Hayes A. Kenner GW. Williams NR. J. Chem. Soc. 1958, 3779

12a Tabushi I. Kitaguchi H. In Synthetic Reagents Vol. 4: Pizey JS. Wiley; New York: 1981. p.336

12b Scarsella M. Sleiter G. Gazz. Chim. Ital. 1988, 118: 757

12c Paine JB. Dolphin D. J. Org. Chem. 1988, 53: 2787

12d Okada K. Saburi K. Nomura K. Tanino H. Tetrahedron 2001, 57: 2127

12e Diaz L. Buldain G. Frydman B. J. Org. Chem. 1979, 44: 973

13a Corwin AH. Straughn JL. J. Am. Chem. Soc. 1948, 70: 1416

13b Mackman RL. Micklefield J. Block MH. Leeper FJ. Battersby AR. J. Chem. Soc., Perkin Trans. 1 1997, 2111

14a Corwin AH. Bailey WA. Viohl P. J. Am. Chem. Soc. 1942, 64: 1267

14b Rezzano I. Buldain G. Frydman B. J. Org. Chem. 1982, 47: 3059

14c Richert C. Wessels JM. Müller M. Kisters M. Benninghaus T. Goetz AE. J. Med. Chem. 1994, 37: 2797

14d Vogel E. Balci M. Pramod K. Koch P. Lex J. Ermer O. Angew. Chem. 1987, 909

15a Thompson A. Dolphin D. J. Org. Chem. 2000, 65: 7870

15b Jiao W. Lash TD. J. Org. Chem. 2003, 68: 3896

16 Smith KM. Craig GW. Eivazi FE. Martynenko Z. Synthesis 1980, 493

17a Gennari C. Longari C. Ressel S. Salom B. Mielgo A. Eur. J. Org. Chem. 1998, 945

17b Dyke H. Steel PG. Thomas EJ. J. Chem. Soc., Perkin Trans 1 1989, 525

17c Neipp CE. Martin SF. J. Org. Chem. 2003, 68: 8867

18 Brown MJ. Carter PS. Fenwick AE. Fosberry AP. Hamprecht DW. Hibbs MJ. Jarvest RL. Mensah L. Milner PH. O’Hanlon PJ. Pope AJ. Richardson CM. West A. Witty DR. Bioorg. Med. Chem. Lett. 2002, 12: 3171

19 Zkatoidsky P. Helv. Chim. Acta 1994, 77: 150

20 Fujiwara T. Kato Y. Takeda T. Tetrahedron 2000, 56: 4859

21a Smith KM. Pandey RK. J. Heterocycl. Chem. 1983, 20: 1383

21b Johnson AW. Kay IT. Markham E. Price R. Shaw KB. J. Chem. Soc. 1959, 3416

22 A similar oxidation of 15 to 16 using lead tetraacetate is mentioned in ref. 5. But the synthetic procedure is more complicated, for example requiring careful drying of the lead tetraacetate. Furthermore oxidation with SO₂Cl₂ is also described in the literature, but without isolation or characterization of 16 and with an overall yield (until the next isolated intermediate) of only 10%: Clezy PS. Hai TT. Gupta PC. Aust. J. Chem. 1976, 29: 393