An azomethine ylide approach to complex alkaloid-like heterocycles |
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Authors: | Murray William V Francois David Maden Amy Turchi Ignatius |
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Affiliation: | Johnson and Johnson Pharmaceutical Research and Development LLC, 8 Clarke Drive, Cranbury, New Jersey 08512, USA. wmurray@prdus.jnj.com |
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Abstract: | The nitrone above is readily available via the intramolecular aza Diels-Alder reaction of an amino acid derived triene in acetic acid. Subsequent treatment of the nitrone in refluxing toluene with substituted actetylenes produced the pictured pyrrole. At lower temperatures a 2,3-dihydroisoxazole, which is the product of a 3+2 dipolar cycloaddition, is produced. Upon heating in refluxing toluene the 2,3-dihydroisoxazole is converted to the pyrrole. |
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