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1967, 390; A. R. Battersby, R. B. Herbert, L. Pijewska, and F. , 1965, 228; A. R. Battersby and R. B. Herbert, Proc. Chem. , 1964, 260; A. R. Battersby, Pure Appl. , 1967, 14, 117; D. Gross, in ref. 15, p. 359. A. R. Battersby, R. B. Herbert, L. Pijewska, F. Santavy, and P. S. Perkin I, 1972, 1736. A. R. Battersby, T. A. Dobson, D. M. Foulkes, aod R. B. S. Perkin I , 1972, 1730. A. R. Battersby, R. B. Herbert, E. McDonald, R. Ramage, and J. H. S. Perkin I, 1972, 1741. (a) A. R. Battersby and J.
Mothes, K. Winkler, D. Groger, H. G. Floss, U. Mothes, and F. Weygand, Tetrahedron Letters, 1962,933; R. Voigt, M. Bornschein, and G . Rabitzsch, Pharmazie, 1967, 22, 326. S. Agurell and M. Johansson, Acta Chem. , 1964, 18, 2285; H. G. Floss, H. Giinther, D. Groger, and D. Erge, 2. , 1966, 21b, 128. The Alkaloids 34 L-Valine CO,H H H (129) Lysergic Acid (130) + 0 MeN 7)- -. N -- 0 H 0 "A / of lysergic acid is incorporated into lysergic acid amides but it is a less efficient precursor than lysergic acid (129) and the double bond isomerization also occurs spontaneously.
P. Tiwari, J. Chern. SOC,( C ) , 1966, 676. I. T. Bruce and G. W. Kirby, Chem. , 1968, 207; Chimia ( S w i t z . ) ,1968,22,314. W. C. Wildman and N. E. Heimer, J . Amer. Chem. ,1967, 89, 5265. C. Fuganti and M . S. Chem. , 1972, 936. Biosynthesis 25 [ 1-’4C]-O-methylnorbelladine[as (88)] with equal tritium labelling of positions 3‘, 5’, and 5” was incorporated into lycorine with retention of the C-5” tritium label only. Further, [ h 3 H; 5-’4C]caranine [as (92)] was incorporated into lycorine (93) with high retention of tritium and this label was shown to be located at C-2.
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