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Pyrrolizidine alkaloid biosynthesis synthesis of 4 carbon 14 n 4 aminobutyl 1 2 didehydropyrrolidinium and its incorporation into different pyrrolizidine bases necines



Pyrrolizidine alkaloid biosynthesis synthesis of 4 carbon 14 n 4 aminobutyl 1 2 didehydropyrrolidinium and its incorporation into different pyrrolizidine bases necines



Journal of the Chemical Society Perkin Transactions I (8): 2003-2008



N-([4-14C]-4-Aminobutyl)-1,2-didehydropyrrolidinium chloride hydrochloride 19 was prepared from the mesylate of 3-chloropropanol by displacement of the mesylate with sodium [14C]cyanide, nucleophilic substitution of the chloro group by pyrrolidine, reduction of the nitrile and oxidation of the amine with mercuric acetate. This material was fed together with [2,3-3H]putrescine dihydrochloride to Senecio isatideus which produces retrorsine 6, Senecio pleistocephalus which makes rosmarinine 11, Cynoglossum officinale which contains echinatine 8 and Cynoglossum asustrale which produces cynaustraline 13 and cynaustine 15. Comprison of the 3H/14C ratios of the precursor mixtures with the alkaloids obtained after the feeding experiments had been carried out showed that the 14C-labelled immonium ion 19 is an efficient precursor for all the different base portions (necines) of the five pyrrolizidine alkaloids. The presence of the immonium ion 3 in Senecio pleistocephalus was established by an intermediate trapping experiment. Thus the immonium ion 3 is involved in the biosynthetic pathways to a range of necines, including retronecine 5, heliotridien 7, rosmarinecine 10, (+)-isoretronecanol 12 and (+)-supinidine 14.

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