title: Parallel synthesis of a desketoraloxifene analogue library via iodocyclization/palladium-catalyzed coupling.
abstract: For a future structure-activity relationship (SAR) study, a library of desketoraloxifene analogues has been prepared by parallel synthesis using iodocyclization and subsequent palladium-catalyzed coupling reactions. Points of desketoraloxifene diversification involve the two phenolic hydroxyl groups and the aliphatic amine side chain. This approach affords oxygen-bearing 3-iodobenzo[b]thiophenes 4 in excellent yields, which are easily further elaborated using a two-step approach involving Suzuki-Miyaura and Mitsunobu coupling reactions to give multimethoxy-substituted desketoraloxifene analogues 6. Various hydroxyl-substituted desketoraloxifene analogues 7 were subsequently generated by demethylation with BBr(3).
authors: Department of Chemistry, Iowa State University, Ames, 50011, United States.
authors: Chul-Hee
authors: CH
authors: Cho
authors: Dai-Il
authors: DI
authors: Jung
authors: Benjamin
authors: B
authors: Neuenswander
authors: Richard C
authors: RC
authors: Larock
mesh_terms: D002384:Catalysis; D060326:Chemistry Techniques, Synthetic; D003500:Cyclization; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*; D054852:Small Molecule Libraries / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism; D013876:Thiophenes / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D054852:Small Molecule Libraries; D013876:Thiophenes; D010165:Palladium