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Synthesis 2010(10): 1707-1711
DOI: 10.1055/s-0029-1218735
DOI: 10.1055/s-0029-1218735
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New YorkThe Meldrum’s Acid Route to Prodigiosin Analogues
Weitere Informationen
Received
15 February 2010
Publikationsdatum:
09. April 2010 (online)
Publikationsverlauf
Publikationsdatum:
09. April 2010 (online)

Abstract
3-Methoxy-5-(2-thienyl)thiophene-2-carboxaldehyde and 3-methoxy-l-methyl-5-(2-thienyl)pyrrole-2-carboxaldehyde were prepared from the appropriate 3-hydroxypyrrole or 3-hydroxythiophene by regioselective O-alkylation and formylation. Condensation of these aldehydes with activated pyrroles in the presence of phosphoryl chloride provides analogues of prodigiosin, which differ from the natural products in the nature of the heteroatoms.
Key words
gas-phase reactions - heterocycles - pyrroles - prodigiosins
- 1 Review:
Fürstner A. Angew. Chem. Int. Ed. 2003, 42: 2582 - For example:
- 2a
Rapoport H.Holden KG. J. Am. Chem. Soc. 1962, 84: 635Reference Ris Wihthout Link - 2b
Boger DL.Patel M. J. Org. Chem. 1988, 53: 1405Reference Ris Wihthout Link - 2c
Wassermann HH.Petersen AK.Xia M.Wang J. Tetrahedron Lett. 1999, 40: 7587Reference Ris Wihthout Link - 3a
D’Allessio R.Rossi A. Synlett 1996, 513Reference Ris Wihthout Link - 3b
D’Allessio R.Bargiotti A.Carlini O.Calotta F.Ferrari M.Gnocchi P.Isetta A.Monelli N.Rossi A.Rossi M.Tibolla M.Vanotti E. J. Med. Chem. 2000, 43: 2557Reference Ris Wihthout Link - 4a
McNab H.Monahan LC. J. Chem. Soc., Perkin Trans. 1 1988, 863Reference Ris Wihthout Link - 4b Review:
McNab H.Monahan LC. In Pyrroles Vol. 2:Jones RA. Wiley; New York: 1992. p.525Reference Ris Wihthout Link - 4c Review:
Gaber AM.McNab H. Synthesis 2001, 2059Reference Ris Wihthout Link - 5
McNab H.Hunter GA. J. Chem. Soc., Perkin Trans. 1 1995, 1209 - 6
Blake AJ.Hunter GA.McNab H. J. Chem. Soc., Chem. Commun. 1990, 734 - 7
Fürstner A.Grabowski EJ. ChemBioChem 2001, 2: 706 - 8
Hunter GA.McNab H.Monahan LC.Blake AJ.
J. Chem. Soc., Perkin Trans. 1 1991, 3245 - 9
Derbyshire PA.Hunter GA.McNab H.Monahan LC. J. Chem. Soc., Perkin Trans. 1 1993, 2017 - 10a
Bellamy F.Martz P.Streith J. Heterocycles 1975, 3: 395Reference Ris Wihthout Link - 10b
Bellamy F.Streith J.Fritz H. Nouv. J. Chim. 1979, 3: 115Reference Ris Wihthout Link - 10c
Bellamy F.Streith J. J. Chem. Res., Synop. 1979, 18 ; J. Chem. Res., Miniprint 1979, 101Reference Ris Wihthout Link - 11
Wasserman HH.Rodgers GC.Keith DD. Tetrahedron 1976, 32: 1851 - 12 For example:
Castro AJ.Deck JF.Hugo MT.Lowe EJ.Marsh JP.Pfeiffer RJ. J. Org. Chem. 1963, 28: 857 - 13
van Koeveringe JA.Lugtenburg J. Recl. Trav. Chim. Pays-Bas 1977, 96: 55 - 14
Jenkins S.Incarvito CD.Parr J.Wasserman HH. CrystEngComm 2009, 11: 242 - 15
Hill L.Hunter GA.Imam SH.McNab H.O’Neill WJ. Synthesis 2009, 2531 - 16
Heaney H.Ley SV. J. Chem. Soc., Perkin Trans. 1 1973, 499 - 17
Barrero AF.Sanchez JF.Oltra JE.Teva D.
J. Heterocycl. Chem. 1991, 28: 939 - 18a
Vaughn TH.Vogt RR.Nieuwland JA. J. Am. Chem. Soc. 1934, 56: 2120Reference Ris Wihthout Link - 18b
Boekelheide V.Linn WJ. J. Am. Chem. Soc. 1954, 76: 1286Reference Ris Wihthout Link - 19
Williamson NR.Simonsen HT.Ahmed RAA.Goldet G.Slater H.Woodley L.Leeper FJ.Salmond GPC. Mol. Microbiol. 2005, 56: 971