Synthesis of 3,4-fused cycloalkanopyrroles by 1,3-dipolar cycloaddition |
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Authors: | James M. Kelly Finian J. Leeper |
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Affiliation: | Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge CB2 1EW, UK |
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Abstract: | The synthesis of a number of 3,4-fused cycloalkanopyrroles bearing substituents on the cycloalkane ring was accomplished by 1,3-dipolar cycloaddition. The yield of the cyclization appeared to depend on the base-sensitivity of the Michael acceptor, but the method is applicable across a broad range of cyclic α,β-unsaturated ketone esters. Functional group transformations can be undertaken following pyrrole synthesis to increase the diversity of cycloalkanopyrroles accessible by this method. One pyrrole thus made is a diester of a conformationally-constrained analogue of porphobilinogen, the precursor of the natural tetrapyrroles. |
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