Organic Letters · 2014 · 22 citations · 18 references
PharmacyChemistryMedicinal ChemistryDrug DiscoveryMolecular PharmacologySynthetic Medicinal ChemistryHeterocycle SynthesisOrganic SynthesisRetrosynthetic AnalysisEpidermal Growth Factor Receptor InhibitionEpidermal Growth Factor Receptor SignalingNatural Product Total SynthesisRadical CyclizationRing-forming ReactionsTotal Synthesis-derived AnaloguesTyrosine Kinase InhibitionTyrosine Kinase Receptors
A new synthetic route to clavilactone B, a naturally occurring inhibitor of epidermal growth factor receptor (EGFR) tyrosine kinase, is disclosed. The route features a sequential samarium-mediated radical cyclization-fragmentation of an indanone derivative, which provides rapid access to a 10-membered carbocyclic motif fused to an aromatic ring.
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Sequenced reactions with samarium(II) iodide
Gary A. Molander, Christina R. Harris · Tetrahedron · 1998 · 349 citations