Azomethine ylide cycloaddition/reductive heterocyclization approach to oxindole alkaloids: Asymmetric synthesis of (-)-horsfiline

G. Cravotto, G. B. Giovenzana, T. Pilati, M. Sisti, G. Palmisano

Risultato della ricerca: Contributo su rivistaArticolo in rivistapeer review

Abstract

The intermolecular [3 + 2] with 2(2-nitrophenyl)acrylate dienophiles followed by reductive heterocyclization affords the spiro(indole-pyrrolidine) ring system. Hence, this enable us to accomplish a concise and highly enantioselective synthesis of (-)-horsfiline 1, based on chiral auxiliary-directed π-face discrimination in the 1,3-dipolar cycloaddition of (1S,2R)- 2-phenyl-1-cyclohexyl ester 4f with N-methylazomethine ylide.

Lingua originaleInglese
pagine (da-a)8447-8453
Numero di pagine7
RivistaJournal of Organic Chemistry
Volume66
Numero di pubblicazione25
DOI
Stato di pubblicazionePubblicato - 14 dic 2001

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