Four stereoisomers of 1,2-epoxy-3-hydroxyerythrinans are synthesized and their stereochemistries determined unambiguously. Of these, the 1,2α-epoxy-3α-alcohol 4 is converted to the alkenoid-type alkaloid, (±)-erythratidine 1, utilizing reductive migration of an α,β-unsaturated γ,δ-epoxyamide with samarium diiodide as a key step.
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Hosoi et al. (2000) studied this question.
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