Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2006(1): 89-96
DOI: 10.1055/s-2005-918435
DOI: 10.1055/s-2005-918435
PAPER
© Georg Thieme Verlag Stuttgart · New York
Synthesis of Orthogonally Protected Pyrrole Tricarboxylic Acid Derivatives: Versatile Building Blocks for Pyrrole-Containing Compounds
Further Information
Received
11 May 2005
Publication Date:
25 October 2005 (online)
Publication History
Publication Date:
25 October 2005 (online)
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
-
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