ETD Collection

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Author: search.filters.author.Cheesman, Penelope, SueSubject: search.filters.subject.Organic compounds--Synthesis

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    The synthesis of 3,5-disubstituted indolizidines
    (1996) Cheesman, Penelope, Sue
    Aspects of the literature of the ant venom alkaloid monomorine I and its stereoisomers were reviewed. Racemic 5-butyl-2-pyrrolidinone was synthesised in two steps from methyl acrylate and 1-nitropentane, A thionation step yielded 5-butylpyrrolidine-2-thione. The Michael addition reaction between 5-butylpyrrolidine-2-thione and ethyl crotonate proceeded with difficulty to form a separable mixture of diastereomers of 5-butyl-l-(2-ethoxycarbonyl-l-methylethyl) pyrrolidine-2-thione. [Abbreviated Abstract. Open document to view full version]