Total synthesis of indole and dihydroindole alkaloids. XVII. The total synthesis of catharine and vinamidine (catharinine)
- 1 July 1979
- journal article
- research article
- Published by Canadian Science Publishing in Canadian Journal of Chemistry
- Vol. 57 (13) , 1682-1690
- https://doi.org/10.1139/v79-270
Abstract
Oxidation of 16,18-dicarbomethoxycleavamine gave the epoxide (6) and the enamide (9). Similar oxidation of 3′,4′-dehydrovinblastine (8) or leurosine (7) gave the natural product catharine (3). Potassium permanganate oxidation of 7 or 8 gave 3R-hydroxyvinamidine (19) whereas similar oxidation of 4′-deoxyleurosidine (29) gave the alkaloid vinamidine (4).This publication has 3 references indexed in Scilit:
- Total synthesis of indole and dihydroindole alkaloids. XVI. Derivatives of vinblastine and vincristine: change of functionality in the vindoline unitCanadian Journal of Chemistry, 1978
- Structure de la catharinine: “alcaloïde” bis-indolique isolé de plusieurs espèces de catharanthusTetrahedron, 1978
- Total synthesis of indole and dihydroindole alkaloids. XII. Selective functionalization of various bisindoles. Efficient syntheses of leurosine and related bisindole alkaloid derivativesCanadian Journal of Chemistry, 1978