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Alcaloides Indoliques. V. Structure de la Voacarpine

par Tournay, Monique ;Pecher, Jacques ;Martin, Ricardo;Friedmann‐Spiteller, Margot;Spiteller, Gerhard
Référence Bulletin des Sociétés chimiques belges, 74, 3-4, page (170-186)
Publication Publié, 1965

Article révisé par les pairs

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Résumé :

Voacarpine, a minor alkaloid obtained from Voacanga chalotiana Pierre ex Stapf (Apocynaceae), is shown to have the tautomeric structure VII ⇆ VIII. The non basic O,N‐diacetyl‐ and O,N‐ditosyl derivatives are true 2‐acyl‐indoles (IX, X). Isovoacarpine, isomeric with voacarpine, is obtained by acid treatment followed by neutralization; it is also a carbinolamine compound. On acetylation, it gives a monoacetyl derivative. UV, IR, NMR and mass spectra of voacarpine and derivatives are discussed. Copyright © 1965 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim