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Alcaloides Indoliques. VII. Structure de la Voacoline

par Lhoest, Georges J J G.;De Neys, Robert ;Defay, Nicole ;Seibl, Josef;Pecher, Jacques ;Martin, Ricardo
Référence Bulletin des Sociétés chimiques belges, 74, 11-12, page (534-550)
Publication Publié, 1965

Article révisé par les pairs

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Résumé :

Voacoline, a new minor alkaloid from Voacanga chalotiana Pierre ex Stapf (apocynaceae) is shown to have structure I. This structure contains two unusual features : a Na‐CH3 indolic group and a hemiketal function. This last feature accounts for the very easy formation of O‐methyl II and O‐ethyl‐voacoline HI. A correlation with voachalotine IV, the major alkaloid of the same species, has been achieved by degradation of I to dihydrodeshydroxymethylvoachalotine XIV. UV, IR, NMR and mass spectra of I and some of its derivatives are discussed. Copyright © 1965 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim