By Maurice Shamma
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Extra info for Isoquinoline Alkaloids Research 1972–1977
Example text
Somniferum L. 11. 11 (+ )-Norreticuline is not a precursor for papaverine. 58 • 59 The problem of the ease of N-demethylation in Papaver species is stilI not completely solved since labeled (± )-reticuline was not incorporated in papaverine while (+)laudanosoline, which possesses the same absolute configuration as (- )-norlaudanosoline, was incorporated. 58 It is known that in some cases N-demethylation definitely does occur since morphine is metabolized to normorphine. 60 It has been claimed that norlaudanosoline is present in nanogram quantities in rat brain following chronic administration of ( - )-dopa.
Kametani and T. Okawara, J. Chern. Soc. Perkin 1,579 (1977). 31. H. B. Kagan, N. Langlois, and T. P. Dang, J. Organornetal. , 90, 353 (1975). 32. L. Simon and G. Talpas, Pharrnazie, 29, 314 (1974). For the use of thioureas and thioamides in the Bischler-Napieralski cyc1ization, see A. A. B. Hazzaa, A. M. M. E. Omar, and M. S. Ragab, Pharrnazie, 28, 364 (1973); and M. S. Ragab, A. M. M. E. Omar, and A. A. B. Hazzaa, Pharrnazie, 29, 178 (1974). Alkyl or aryl thiocyanates can also be used in conjunction with phenacetyl chlorides, see M.
Marchelli, and H. Coda de Lorenzo, Tetrahedron, 28, 5999 (1972). 28a. T. Kametani, K. Kigasawa, M. Hiiragi, H. Ishimaru, and K. Shiroyama, J. Pharrn. Soc. Japan, 96, 1031 (1976). 29. J. Sandrin, D. Soerens, L. Hutchins, E. Richfield, F. Ungemach, and J. M. Cook, Heterocycles, 4, 1101 (1976). 30. T. Okawara and T. Kametani, Heterocycles, 2, 571 (1974); and T. Kametani and T. Okawara, J. Chern. Soc. Perkin 1,579 (1977). 31. H. B. Kagan, N. Langlois, and T. P. Dang, J. Organornetal. , 90, 353 (1975).