Alkaloids: Chemistry and Pharmacology, Volume 12 by R.H.F Manske, H.L. Holmes

By R.H.F Manske, H.L. Holmes

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Additional resources for Alkaloids: Chemistry and Pharmacology, Volume 12

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It was first believed that in the periodate oxidation of XLIII, 3 moles of NaI03 was consumed and this led to the conclusion that XLIII contains four adjacent hydroxyls (19),an assumption later shown to be incorrect by the same authors (37). Apparently, ~ ~ 22 S. W. PELLETIER AND L. H. KEITH due to the high alkalinity of solutions of XLIII, other groups in addition to the glycol were oxidized. A subsequent oxidation under neutral conditions led to consumption of only 2 moles of periodate, giving amphoteric uncrystallizable products.

A large part of the initial chemical elucidation of the structure of aconitine was based on oxonitine, a permanganate oxidation product of aconitine. Oxonitine was first formulated by Jacobs et al. (77) as C33H43N012 and later (78) as C34H45N012. The uncertainty regarding the formulation of oxonitine has centered mainly on whether the compound contains an N-acetyl or an N-formyl group. The later microanalysis data suggested that the oxidation proceeded without loss of a carbon atom, thus yielding an N-acetyl compound.

This independent study not only substantiated the previous structural elucidation by chemical means but also eliminated &T-‘&y; OH OAc RO OCH3 OCH3 CXXIa; R = H, R’ = CH3 CXXIb; R = CH3, R’ = H ; OCH3 OCH3 CXXII the ambiguity of the methoxyl and hydroxyl positions in ring A, as well as providing the absolute and relative configurations of 13 out of the 15 asymmetric centers present in aconitine. A large part of the initial chemical elucidation of the structure of aconitine was based on oxonitine, a permanganate oxidation product of aconitine.

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