By R.H.F Manske, H.L. Holmes
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Extra resources for Alkaloids: Chemistry and Pharmacology, Volume 12
While there is no rigorous proof of the configuration of the C-7 hydroxyl VI; R = H 2 XXI xx: R = O xxv ~ ~ ~ 14 S . W . PELLETIER AND L. H. KEITH in VIII, it is most likely trans to the C-6 methoxyl since the diacetate X I was observed to lose acetic acid slowly when sublimed. Edwards et al. (13)deduced the correct structure of hydroxylycoctonine from a study of isolycoctonine (XII). The latter is formed by hydrogenation of hydroxylycoctonine over platinum and contains a seven-membered ketone.
It was therefore plausible OCH3 CXXXIVb; R = Bz CXXXVII; R = H cxxxv CXXXVI ~ ~ 44 S. W. PELLETIER AND L. H. This evidence suggested that the C-8 acetoxy group and the (2-15hydroxyl of aconitine may be trans. The ketonic nature of pyrooxonitine was spectroscopically shown by the presence of a carbonyl cxxxvIII CXLIX CXXXIX CXL absorption band characteristic of a cyclic six-membered ketone (1718 cm-1) in pyrooxonine (CXXXVII), the hydrolysis product of pyrooxonitine (CXXXIVb), and also by the peak typical for ketones a t 343 mp ([a]- 1020°) in the ORD curve of pyrooxonitine.
Acid isomerizes oxodelpheline (LXIX) to isooxodelpheline (LXX), which contains a tertiary liydroxyl in place of the secondary one in LXIX. 3Hz) in LXX indicates a six-membered methylenedioxy ring, which is consistent with the tentative structure previously proposed for this compound (29). The biosynthetic incorporation of mevalonic acid into a natural product is frequently used to test whether the substance is of terpenoid origin. elatum were fed with dl-(14C-2)mevalonic acid and, surprisingly, the delpheline isolated had no detectable radioactivity.