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

G Cravotto, GB Giovenzana, T Pilati…

Index: Cravotto; Giovenzana; Pilati; Sisti; Palmisano Journal of Organic Chemistry, 2001 , vol. 66, # 25 p. 8447 - 8453

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Citation Number: 125

Abstract

The intermolecular [3+ 2] annulation of azomethine ylides 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 (1 S, 2 R)-2-phenyl-1-cyclohexyl ester 4f with N- ...