Pyrrole-singlet oxygen reactions leading to α,α'-bipyrroles. Synthesis of prodigiosin and analogs

Tetrahedron Letters

Volumn 40, Issue 43, 1999, Pages 7587-7589

  Wasserman, Harry H ^a   Petersen, Anders K ^a   Xia, Mingde ^a   Wang, Jianji ^a  

^a YALE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOXYLIC ACID DERIVATIVE; DRUG ANALOG; HYDROPEROXIDE; PRODIGIOSIN; PYRROLE DERIVATIVE; SINGLET OXYGEN;

ARTICLE; CHEMICAL MODIFICATION; DRUG SYNTHESIS; MOLECULAR INTERACTION;

EID: 0033595888     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01538-5     Document Type: Article

References (16)

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2. Wasserman, H. H.; Xia, M.; Wang, J.; Petersen, A. K.; Jorgensen, M. R. Tetrahedron Lett. 1999, 40, 6145.
3. Hydroperoxides related to compound 2 have been isolated from the methylene blue sensitized photooxidation of 2,5-di-t-butylpyrrole and 2,3,5-tri-t-butylpyrrole. Ramasseul, R.; Rassat, A. Tetrahedron Lett. 1972, 1337.
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12. (c) Wasserman, H. H.; Rodgers, G. C.; Keith, D. D. Tetrahedron 1976, 32, 1851.
13. 6 discloses a novel pathway to undecylprodigiosin by a Suzuki cross-coupling of two pyrrole rings.
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15. +: 296.1763. Found: 296.1760.
16. Recent work on the incorporation of a thiophene residue in the framework of a prodigiosin analog has been reported: Blake, A. J.; Hunter, G. A.; McNab, H. J. Chem. Soc., Chem. Commun. 1990, 734.