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Intramolecular cycloadditions of azides with olefins: Synthetic approaches to pyrrolizidine and indolizidine alkaloids

Posted on:1992-01-06Degree:Ph.DType:Dissertation
University:University of MichiganCandidate:Williams, John PatrickFull Text:PDF
GTID:1471390017950028Subject:Chemistry
Abstract/Summary:
Alkyl azides were found to undergo intramolecular cycloadditions with various olefins to provide 4,5-dihyro-3H-pyrroles, 2,3,5,6,7,7a-hexahydro-1H-pyrrolines (pyrrolizidines) and 1,2,3,5,6,7,8,8a-octahydroindolizines (indolizidines). Thermolysis of racemic mixtures of (Z)-7-azido-5-(methoxy)methoxy-3-phenylthio-1,3-heptadiene and (Z)-8-azido-5-(methoxy)methoxy-3-phenylthio-1,3-octadiene provided racemic mixtures of (1R*,7aR*)-2,3,5,7a-tetrahydro-1-(methoxy)methoxy-7-phenylthio-;Heating (S)-5-azido-3- ((benzyl)oxy) methoxypentene, which was derived from (S)-malic acid, at 120...
Keywords/Search Tags:Intramolecular cycloadditions, Racemic mixtures
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