ANODIC C16-C21 FRAGMENTATION OF CATHARANTHINE IN METHANOL - SYNTHESISOF 16-METHOXYCLEAVAMINE

Authors
TABAKOVIC I GUNIC E GASIC MJ
Citation
I. Tabakovic et al., ANODIC C16-C21 FRAGMENTATION OF CATHARANTHINE IN METHANOL - SYNTHESISOF 16-METHOXYCLEAVAMINE, Perkin transactions. 2, (12), 1996, pp. 2741-2745
Citations number
25
Categorie Soggetti
Chemistry Physical","Chemistry Inorganic & Nuclear
Journal title
Perkin transactions. 2 → ACNP
ISSN journal
03009580
Issue
12
Year of publication
1996
Pages
2741 - 2745
Database
ISI
SICI code
0300-9580(1996):12<2741:ACFOCI>2.0.ZU;2-7
Abstract
Two-electron controlled potential oxidation of catharanthine (Cath) af fords 2 in 65% yield, Compound 2 is reduced to 16-methoxycleavamine in 95% yield, Cyclic voltammetry experiments show that catharanthine hyd rochloride (CathH(+)) in methanol solution in the presence of 2,6-luti dine exists in acid-base equilibrium with Cath as a free base which is oxidized at 0.7 V vs, SCE, Oxidation of Cath to Cath(+) and fragmenta tion of the C16-C21 bond is assumed to occur via a concerted mechanism .