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E. Tyler, and E. Ramstad, Chem. , 1970, 775; R. B. Herbert, in ref. 14, p. 28. D. Groger and P. Sajdl, Pharmazie, 1972,27, 188; R. Voigt and P. , p. 186. R . Voigt and P. Zier, Pharmazie, 1972, 27, 773. T. Fehr, W. Acklin, and D. Arigoni, Chem. , 1966,801 ; H. G. Floss, U. Hornemann, N. Schilling, D. Groger, and D. Erge, Chem. , 1967, 105. H. G . Floss, G . P. Basmadjian, M. Tcheng, D. Groger, and D. Erge, Lloydia, 1971,34, 446; R. B. Herbert, in ref. 2, p. 7. T. Ohashi, H. Takahashi, and M. Abe, Nippon N6gei Kagaku Kaishi, 1972,46, 5 3 5 .
Biosynthesis 21 proved to be of singular significance5* Manifestly it appeared to be the product of phenol-coupling of the phenethylisoquinoline (76). Furthermore, a close relationship between androcymbine (72) and the dienone (68) could be seen, and so the earlier hypothetical route to colchicine could be tentatively modified to (76) + (77) + (70). Hydroxylation of (77) could provide the starting point for ring expansion. autumnale and C. byzantinurn. 60 [''NlTyrosine was also incorporated into the alkaloid in accord with the expected derivation of the amino-function of colchicine from that of tyrosine.
Biol. 1972, 10, 101 (Chem. , 1973, 78, 13 761j).