Copper-Catalyzed Cyclization/Dimerization of Tryptamines with O2/Air as the Sole Oxidant: Direct Access to Complex Bispyrrolidino[2,3-b]indoline.
J Org Chem
; 86(23): 17164-17172, 2021 12 03.
Article
em En
| MEDLINE
| ID: mdl-34709032
ABSTRACT
The first transition metal catalytic one-step synthesis of the 3a, 3a'-bispyrrolidino [2,3-b] indoline scaffold via tandem cyclization/dimerization of tryptamines has been realized with the environmentally friendly O2/air as the sole oxidant. Different from the traditional direct oxidation of indole "N-H" group by excess amount of metal salts, a copper-catalyzed oxidative cyclization reaction is developed for the formation of the radical pyrrolidinoindoline intermediate in the current strategy. The robustness and practicality of this methodology is demonstrated by the step-economic, divergent total synthesis of natural products (±)-folicanthine and meso-folicanthine.
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1
Base de dados:
MEDLINE
Assunto principal:
Triptaminas
/
Cobre
Idioma:
En
Ano de publicação:
2021
Tipo de documento:
Article