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Extra resources for Chemistry and Physiology
These epimers were hydrolyzed to the crystalline compound C22H33N06when treated with aqueous sulfuric acid. This compound formed a tetraacetate derivative for which structure 105 was Proposed on the basis of spectral data. Oxidation of excelsine with Kiliani reagent gave a compound (C22H31N06) containing a five-membered ring ketone. Under similar conditions, lappaconine and lapaconidine also gave five-membered ring 36 S. WILLIAM PELLETIER AND NARESH V. MODY ketones. Oxidation of excelsine with periodic acid at room temperature furnishes another compound (C22H33N06) with an oxocyclopentyl moiety.
9 ppm in 122,respectively. All other remaining signals were in complete agreement with the assigned structure (122)for sachaconitine. Sachaconitine and karakoline (108) constitute an additional example of a C-1 a-hydroxyl-methoxyl pair along with the other known pairs, neoline-chasmanine, isotalatizidine-talatizamine, and lapaconidine-lappaconine. This additional example suggests the possible existence of other such pairs in nature. Z. ACONOSINE Aconosine (C22H35N04;mp 148") has been isolated by Soviet chemists from A.
The chemical correlation of cammaconine with isotalatizidine demonstrated the presence of a tertiary hydroxyl group at C-8 and a secondary hydroxyl group at C-14 in cammaconine. Thus, because it had been established that the hydroxyl group is not present at C-18, and to avoid identity with isotalatizidine, cammaconine must be represented by structure 69 (95). It is interesting to note that cammaconine is the first example of an aconitine-type alkaloid with a P-hydroxyl group at the C-16 position instead of the usual p-methoxyl group.