The eburnamine/11-methoxytabersonine binary alkaloid 11 has been synthesized and regioselectively hydroxylated at C-17 to give 13 by means of benzeneseleninic anhydride on the analogy with the behaviour of tabersonine 5a towards the same reagent. The reaction proceeds through the initial formation of a 1-azadiene which suffers nucleophilic attack by water. The hydroxylated dimer 13 has been further elaborated into the eburnamine/vindoline binary alkaloid 16, which resulted identical to the product obtained by direct acid promoted condensation of eburnamine 12 with vindoline 4.
Synthesis of the eburnamine/11-methoxytabersonine binary alkaloid and functionalization at C-17 of the Aspidosperma 'lower half' / B. Danieli, D. Passarella, G. Lesma, G. Palmisano, B. Pyuskyulev. - In: FITOTERAPIA. - ISSN 1971-551X. - 64:6(1993), pp. 495-504.
Synthesis of the eburnamine/11-methoxytabersonine binary alkaloid and functionalization at C-17 of the Aspidosperma 'lower half'
B. Danieli;D. Passarella;G. Lesma;G. Palmisano;
1993
Abstract
The eburnamine/11-methoxytabersonine binary alkaloid 11 has been synthesized and regioselectively hydroxylated at C-17 to give 13 by means of benzeneseleninic anhydride on the analogy with the behaviour of tabersonine 5a towards the same reagent. The reaction proceeds through the initial formation of a 1-azadiene which suffers nucleophilic attack by water. The hydroxylated dimer 13 has been further elaborated into the eburnamine/vindoline binary alkaloid 16, which resulted identical to the product obtained by direct acid promoted condensation of eburnamine 12 with vindoline 4.
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