Alkaloids (v. 9) by Royal Society Of Chemistry

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Org. , 1978, 43, 72. E. B. Sanders, H. V. Secor, and J. I. Seeman, J. Org. , 1978, 43, 324. W. B. Edwards, D. F. Glenn, F. Green, and R. H. Newman, J. , 1978,14,255. E. Leete and S. A. S . Leete, J. Org. , 1978,43,2122. J. I. Seeman, H. V. Secor, J. F. Whidby, and R. L. Bassfield, Tetrahedron Letters, 1978, 1901. T. E. Catka and E. Leete, J. O r g . , 1978, 43, 2125. L. Rondahl, Acta Pharm. Suecica, 1977, 14, 113. B. A. Burke and H . Parkins, Tetrahedron Letters, 1978, 2723. 39Two new bases, euonymine (47)and neo-euonymine (48),have been isolated from the seeds of Euonyrnus sieboldiana Blume.

K. Kaneko, M. W. Tanaka, and H. Mitsuhashi, Phytochemistry, 1977,16, 1247; K. Kaneko, M. Watanabe, and H. , 1973, 12, 1509. 144Taken with other r e ~ ~ l ont the ~ formation ~ ~ ~ of - the ~ nitrogen ~ ~ ring of different alkaloids, it appears that hydroxylation of one of the terminal methyl groups of cholesterol (144) is a first step in steroidal alkaloid biosynthesis, followed by functionalization of C-22 and formation of the nitrogen ring. The formation of the furan ring in alkaloids such as solasodine (145) and soladulcidine (146) may be deduced to be a last step.

M. Abe, T. Ohashi, S. Ohmoto, and T. Tabuchi, Agric. and Biol. , (Japan),1971,35, A l ; T. Ohashi, H. Takahashi, and M. Abe, Nippon Nogei Kugaku Kuishi, 1972,46, 535; R. B. Herbert, in ref. 5, p. 34; in ref. 4, p. 33. g. lysergyl-valine (135) in ergocornine (1 39) biosynthesis], but the ~' such a biosynthetic reaction. An alternative is weight of e v i d e n ~ e l ~ ~ -isI against for lysergic acid to link to a tripeptide. However, L-valyl-L-valyl-L-proline and L-valyl-L-leucyl-L-proline were found to be incorporated into ergocornine (139) and ergokryptine (140), respectively, only after fragmentation into their constituent a m i n o - a c i d ~ .

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