By J.Edwin Saxton, etc.
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Additional info for Alkaloids Volume 4: Specialist Periodical Rep (Specialist Periodical Reports) (v. 4)
G. "~It was s ~ g g e s t e d ' ~that ~ * ' an ~~ important intermediate in the formation of c-nor-D-homo-steroidal alkaloids could be solanidine (140) derivative with an equatorial hydroxy-group at C-12 which could serve as an initiation point for rearrangement. Accordingly the role of solanidine (140)as a precursor for veratramine (1 39) and jervine (138) has been HO lo' lo' K. Kaneko, H. Mitsuhashi, K. Hirayama, and N. Yoshida, Phytochemistry, 1970, 9, 2489; R . B. Herbert, in ref. 2, p. 41.
In Clivia rniniata, however, it has been discovered that hydroxylation of caranine occurs with retention of c~nfiguration,~following the chance observation that [3',5'-3H, ;O-rnethyl-'4C]-O-methylnorbelladine[as (88)l was incorporated into lycorine (93) with complete loss of tritium. These results were confirmed when 67 68 6q 'O 71 '' 73 C. Fuganti and M. Mazza, Chem. , 1971, 1196; R. B. Herbert, in ref. 2, p. 23. C. Fuganti and M. S. Perkin I , 1973, 954. K. R. Hanson, J . Arner. Chem. , 1966, 88, 2731.
H. Ronsch, European J . , 1972,28, 123. Bwsynthesis 19 aiding the ring-opening reaction was therefore suggested. Although the N-methyl label was completely retained in the derived alpinigenin an enormous difference in the level of incorporation of the two precursors was found, which must call into question whether (66) is a normal intermediate. -Results which delineate the biological route to colchicine (70) had been reported, in essence,57 before the appearance of these reviews. But the publication of a series of full paper^^^-^' provides a fresh opportunity to discuss the remarkable pathway by which this non-basic alkaloid arises in Colchicurn.
Alkaloids Volume 4: Specialist Periodical Rep (Specialist Periodical Reports) (v. 4) by J.Edwin Saxton, etc.