title: Enantioselective and regioselective pyrone Diels-Alder reactions of vinyl sulfones: total synthesis of (+)-cavicularin.
abstract: The total synthesis of (+)-cavicularin is described. The synthesis features an enantio- and regioselective pyrone Diels-Alder reaction of a vinyl sulfone to construct the cyclophane architecture of the natural product. The Diels-Alder substrate was prepared by a regioselective one-pot three-component Suzuki reaction of a non-symmetric dibromoarene.
authors.affiliation: Department of Chemistry, Oregon State University, Corvallis, OR 97331 (USA).
authors.forename: Peng
authors.initials: P
authors.lastname: Zhao
authors.forename: Christopher M
authors.initials: CM
authors.lastname: Beaudry
mesh_terms: D002384:Catalysis; D061565:Cycloaddition Reaction; D004988:Ethers, Cyclic / Q000138:chemical synthesis* / Q000737:chemistry; D011753:Pyrones / Q000737:chemistry*; D013237:Stereoisomerism; D013450:Sulfones / Q000737:chemistry*; D000097566:Cyclophanes
chemical_list: D004988:Ethers, Cyclic; D011753:Pyrones; D013450:Sulfones; C513696:cavicularin; D000097566:Cyclophanes; C009873:divinyl sulfone
keywords: Diels-Alder reaction; asymmetric synthesis; catalysis; chirality; cross-coupling