Tetrahedron: Asymmetry

Synthesis of the oxindole alkaloid (−)-horsfiline

…, C Strässler, M Weber, HJ Borschberg

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

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被引用次数: 86

摘要

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 ...