Pyrrolizidine alkaloid biosynthesis. Incorporation of 2-aminobutanoic acid labelled with 13 C or 2 H into the senecic acid portion of rosmarinine and senecionine

IR Stirling, IKA Freer, DJ Robins

Index: Stirling, Iain R.; Freer, Isabel K. A.; Robins, David J. Journal of the Chemical Society - Perkin Transactions 1, 1997 , # 5 p. 677 - 680

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Citation Number: 21

Abstract

(±)-[3, 4-13C2]-2-Aminobutanoic acid 10 and (±)-[3, 4-2H5]-2-aminobutanoic acid 11 are synthesized by alkylating diethyl acetamidomalonate with labelled ethyl iodide followed by acid hydrolysis. These compounds are used to obtain complete labelling patterns for the first time in a necic acid by studying the pyrrolizidine alkaloids rosmarinine 3 and senecionine 1 using NMR spectroscopy. The senecic acid portion 12 of both alkaloids shows equal ...