Journal of the American Chemical Society

The Absolute Configuration of the C8-Atom in the Pyrrolizidine Moieties of the Senecio Alkaloids

R Adams, D Fleš

Index: Adams; Fles Journal of the American Chemical Society, 1959 , vol. 81, p. 5803

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Citation Number: 11

Abstract

(-)-Methyl 2-acetyl-l-pyrrolidineacetate, a degradation product of monocrotaline, was condensed with methylmagnesium iodide to yield (-)-1-(2-hydroxy-2-methylpropy1)-2-(1- hydroxy-1-methylethyl)-pyrrolidine. The same carbinol was prepared from (S)(-)-proline by converting it first to the methyl ester, condensing this ester with methyl bromoacetate, and finally treating the methyl (-)-2-carbomethoxy-1-pyrrolidineacetate with methylmagnesium ...