Laccase-catalyzed coupling of catharanthine and vindoline: an efficient approach to the bisindole alkaloid anhydrovinblastine

The efficient enzyme-catalyzed coupling of the indolic alkaloids catharanthine and vindoline was carried out by exploiting the oxidoreductases laccases and atmospheric oxygen. Following NaBH 4 reduction of the eniminium cationic intermediate, the synthetically useful dimer anhydrovinblastine (AVBL)...

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Bibliographic Details
Published in:Tetrahedron 2009-01, Vol.65 (1), p.312-317
Main Authors: Sagui, Francesca, Chirivì, Cosimo, Fontana, Gabriele, Nicotra, Silvia, Passarella, Daniele, Riva, Sergio, Danieli, Bruno
Format: Article
Language:English
Subjects:
Chemistry
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with only one n hetero atom and condensed derivatives
Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings
Organic chemistry
Preparations and properties
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Summary:The efficient enzyme-catalyzed coupling of the indolic alkaloids catharanthine and vindoline was carried out by exploiting the oxidoreductases laccases and atmospheric oxygen. Following NaBH 4 reduction of the eniminium cationic intermediate, the synthetically useful dimer anhydrovinblastine (AVBL) was isolated and characterized. Several reaction parameters were investigated in detail and, under the optimized reaction conditions, AVBL was isolated in 56% yield. The practicability of this bioconversion was further confirmed through the condensation of catharanthine with the vindoline analogue 11-methoxy-dihydrotabersonine. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2008.10.064