Organic Letters · 2009 · 60 citations · 11 references
PharmacyChemistryMedicinal ChemistryDrug DiscoveryOrganic ChemistrySynthetic Medicinal ChemistryAlkaloid BiosynthesisHeterocycle SynthesisOrganic SynthesisRetrosynthetic AnalysisAlkaloid Skeleton FormationAromatic Nucleophilic SubstitutionElectrophilic Aromatic SubstitutionElectrophilic Substitution In HeterocyclesIminium IonsSpirocyclic Scaffold DiversificationSpirocyclic ScaffoldsSpiroheterocycle Synthesis
A domino process consisting of an amidation, spirocyclization, and formation of an iminium ion and electrophilic aromatic substitution of a phenylethylamine and a ketoester leads to the spirocyclic skeleton of (+)-erysotramidine, which can be further transformed into the natural alkaloid.
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Total Synthesis of (+)‐β‐Erythroidine
Hironori Fukumoto, Keisuke Takahashi, Jun Ishihara et al. · Angewandte Chemie International Edition · 2006 · 67 citations