Vomicine oxidation products

The oxidation of dihydrovomicine gives the dihydroderivatives of CCLXXXIV, CCLXXXV, and CCLXXXVI, which may also be obtained by catalytic hydrogenation of the vomicine oxidation products (207). 

Vomicidine and derivatives, 591, 592 oxidation, 594 Vomicine, 553, 586, 589, 592 constitution, 586 exhaustive methylation, 592 oxidation, 594 pharmacological action, 596 reduction products, 589 and derivatives, formhlae, 587, 593, 595... 

The sodium amalgam (Emde) reduction of vomicine metho salts (CCLIV) in dilute acetic acid gives two products (195, 203) base I, which has structure CCLVII (R = CH3) (202), and base II, the structure of which is not proved (202, 203). Why allylic hydrogenolysis does not occur is not known. Base I is demethylated to a secondary alcohol CCLVII (R = H) (203), which could not be oxidized by the Oppenauer method back to vomicine (202), nor could vomicine be reduced to it. 

The oxidation of vomicine yields three products the acid CCLXXXIV, analogous to dioxonucine dihydrate (Wielands C17 acid, CXXV), the acid CCLXXXV, the analog of carboxyaponucine (Hanssen s Cie acid, CXXVI), and the base CCLXXXVI, which has no analog in strychnine... 

Three crystalline products have been recovered from the oxidation of vomicine (CMH24O4N2) with chromic acid (8, 15), (a) a base, CieHjjOsNj, m.p. 304°, (b) an acid, CnHasOsNa, m.p. 264°, and (c) an acid, C18H24O7N2,... 

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