An azomethine ylide approach to complex alkaloid-like heterocycles.

The Journal of organic chemistry

PubMedID: 17355150

Murray WV, Francois D, Maden A, Turchi I. An azomethine ylide approach to complex alkaloid-like heterocycles. J Org Chem. 2007;72(8):3097-9.
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.