By Royal Society Of Chemistry
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Hartling, Biochem. Physiol. PjYanzen, 1974, 166, 33. H. G. Floss, M. Tcheng-Lin, H. Kobel, and P. Stadler, Experientia, 1974,30,1369;R. B. Herbert, in ref. 6, p. 31. A. Baumert, D. Groger and W. Maier, Experientia, 1977, 33, 881. 2. RehaEek, J. D . Desai, P. Sajdl, and S. Paioutovh, Canad. J. , 1977, 23, 596. K. K. Rao and A. R. Gupta, Indian J. Exp. , 1977, 15, 588. 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.
42Structures for these, and for four bases encountered earlier43 as components of the same plant of Ethiopian origin, have been advanced, largely as a result of mass and (51) 39 40 4' 42 43 R. M. Smith, in 'The Alkaloids, Chemistry and Physiology', ed. R. H. F. Manske, Vol. XVI, Chapter 4, Academic Press, New York, 1977. K. Yamada, K. Sugiura, Y . Shizuri, H. Wada, and Y. Hirata, Tetrahedron, 1977, 33, 1725. K. Yarnada, Y. Shizuri, and Y. Hirata, Tetrahedron, 1978, 34, 1915. L. Crombie, W. M. L.
A. Cordell, Lloydia, 1974, 37, 219. A. R. Battersby, in ref. 1, p. 31. J. Staunton, in ref. 2, p. 1;R. B. Herbert, in ref. 3, p. 1;in ref. 4, p. 30; in ref. 5, p. 25; in ref. 6 , p. 33; in ref. 7, p. 22. R. B. Herbert in ref. 8, p. 27. 86*88 Earlier intermediates are known9*s37s4 to be secologanin (103) and tryptamine (102). Chemical condensation of these compounds affordsvincoside (109) and strictosidine (isovincoside) (104),which are epimeric at C-3. ^^ This has been puzzling because the first terpenoid indole bases to be formed have the 3a configuration.