Tetrahedron: Asymmetry

Synthesis of the oxindole alkaloid (−)-horsfiline

…, C Strässler, M Weber, HJ Borschberg

Index: Pellegrini; Strassler; Weber; Borschberg Tetrahedron Asymmetry, 1994 , vol. 5, # 10 p. 1979 - 1992

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Citation Number: 86

Abstract

Abstract A synthesis of (-)-horsfiline ((-)-1), a metabolite isolated recently from Horsfieldia superba, is described. The diastereoface selectivity of the crucial oxidative rearrangement of chiral tetrahydro-β-carboline precursors into the corresponding oxindoles was investigated in some detail and found to depend critically on the substitution pattern of the aliphatic amino group. These findings were exploited for the preparation of (-)-1, as well as of the ...

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