A directed metalation route to the zwitterionic indole alkaloids. Syntheses of indolo[2,3-a]quinolizine, flavopereirine, flavocarpine, and dihydroflavopereirine

作者: Gordon W. Gribble , David A. Johnson

DOI: 10.1016/S0040-4039(00)96702-9

关键词: BetaineStereochemistryMetalationAlkaloidChemistryFlavopereirineOrganic chemistryQuinolizineEthylene oxideIndole test

摘要: Abstract A protocol involving beta-lithiation of 2-(2-pyridinyl)indoles (4 → 5) and subsequent reaction with bromoacetaldehyde or oxirane has led to syntheses the alkaloids indolo[2,3-a]quinofizine (1), flavopereirine (2), flavocarpine (21), dihydroflavopereirine (24).

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