Singlet oxygen reactions of 3-methoxy-2-pyrrole carboxylic acid tert-butyl esters. A route to 5-substituted pyrrole precursors of prodigiosin and analogs

Reaction of the tert-butyl ester of 3-methoxy-2-pyrrole carboxylic acid with singlet oxygen yields a peroxidic intermediate which undergoes coupling with a range of nucleophiles to yield 5-substituted pyrroles. Among these products are α,α′-bipyrroles which serve as precursors of prodigiosin, includ...

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Bibliographic Details
Published inTetrahedron Vol. 60; no. 34; pp. 7419 - 7425
Main Authors Wasserman, Harry H., Xia, Mingde, Wang, Jianji, Petersen, Anders K., Jorgensen, Michael, Power, Patricia, Parr, Jonathan
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 16.08.2004
Elsevier
Subjects
Bipyrrole
Chemistry
Chemistry, Organic
Physical Sciences
Prodigiosin
Pyrrole
Science & Technology
Singlet oxygen
Bipyrrole
Singlet oxygen
Prodigiosin
Pyrrole
OXIDATION
singlet oxygen
bipyrrole
CHEMISTRY
VICINAL TRICARBONYLS
prodigiosin
pyrrole
PHOTOOXIDATION
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Summary:Reaction of the tert-butyl ester of 3-methoxy-2-pyrrole carboxylic acid with singlet oxygen yields a peroxidic intermediate which undergoes coupling with a range of nucleophiles to yield 5-substituted pyrroles. Among these products are α,α′-bipyrroles which serve as precursors of prodigiosin, including A-ring substituted analogues. Graphic
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2004.05.053