Chemical Science · 2013 · 108 citations · 40 references
Natural SciencesChemistryMedicinal ChemistryBioorganic ChemistryOrganic ChemistrySynthetic Medicinal ChemistryAlkaloid BiosynthesisHeterocyclic ChemistryOrganic SynthesisPhotochemical SynthesisPhotochemistryRetrosynthetic AnalysisAlkaloid Skeleton FormationCascade StereoselectivityIsoxazole ChemistryIsoxazole SynthesisStereoselectivity
The bicyclic isoxazolidine scaffolds are the ubiquitously recurring motifs in alkaloids. Despite of their facile biosynthesises in nature, the laboratory synthesis of these derivatives is still complicated. In this paper, the isoxazolidine derivatives are concisely constructed in one process with excellent stereoselectivity from simple tertiary amines through a C–H activation-retro-aza-Michael-oxidation-cyclization tandem sequence by means of visible-light. This protocol provides a concise approach to dactylicapnosinine derivatives.
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Visible‐Light Photoredox Catalysis
Jun Xuan, Wen‐Jing Xiao · Angewandte Chemie International Edition · 2012 · 2.2K citations