title: An azomethine ylide approach to complex alkaloid-like heterocycles.
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.
authors.affiliation: Johnson and Johnson Pharmaceutical Research and Development LLC, 8 Clarke Drive, Cranbury, New Jersey 08512, USA. wmurray@prdus.jnj.com
authors.forename: William V
authors.initials: WV
authors.lastname: Murray
authors.forename: David
authors.initials: D
authors.lastname: Francois
authors.forename: Amy
authors.initials: A
authors.lastname: Maden
authors.forename: Ignatius
authors.initials: I
authors.lastname: Turchi
mesh_terms: D000470:Alkaloids / Q000737:chemistry*; D001391:Azo Compounds / Q000737:chemistry*; D006576:Heterocyclic Compounds, 4 or More Rings / Q000737:chemistry*; D015394:Molecular Structure; D011758:Pyrroles / Q000138:chemical synthesis / Q000737:chemistry; D013882:Thiosemicarbazones / Q000737:chemistry*
chemical_list: D000470:Alkaloids; D001391:Azo Compounds; D006576:Heterocyclic Compounds, 4 or More Rings; D011758:Pyrroles; D013882:Thiosemicarbazones; C512188:azomethine