Singlet oxygen reactions of 3-methoxy-2-pyrrole carboxylic acid tert-butyl esters. A route to 5-substituted pyrrole precursors of prodigiosin and analogs |
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| Authors: | Harry H. Wasserman Mingde Xia Jianji Wang Anders K. Petersen Michael Jorgensen Patricia Power Jonathan Parr |
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| Affiliation: | Department of Chemistry, Yale University, 225 Prospect Street, New Haven, CT 06520-8107, USA |
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| Abstract: | 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. |
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| Keywords: | Pyrrole Singlet oxygen Prodigiosin Bipyrrole |
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