The Total Synthesis of Senecic and Integerrinecic Acids1

CCJ Culvenor, TA Geissman

Index: Culvenor,C.C.J.; Geissman,T.A. Journal of the American Chemical Society, 1961 , vol. 83, p. 1647 - 1652

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Citation Number: 18

Abstract

The total synthesis of senecic and integerrinecic acids, the esterifying acids present in the pyrrolizidine alkaloids senecionine and integerrimine, is described. Methyl 2-methylene-3- acetoxybutanoate and ethyl methylacetoacetate were condensed to give a mixture of cis- and trans-5-rnethyl-2-hepten-6-one-3-carboxylic acids. Hydrolysis of the cyanohydrin of the tram isomer gave (+)-integerrinecic acid, which was resolved by means of the brucine ...