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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
Azomethine ylide cycloaddition/reductive heterocyclization approach to oxindole alkaloids: asymmetric synthesis of
G Cravotto1, G B Giovenzana, T Pilati
1Dipartimento di Scienza e Tecnologia del Farmaco, Università di Torino, via Giuria 9, 0125 Torino, Italy.
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 pi-face discrimination in the 1,3-dipolar cycloaddition of (1S,2R)-2-phenyl-1-cyclohexyl ester 4f with N-methylazomethine ylide.
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