title: Total synthesis of (±)-cavicularin: control of pyrone Diels-Alder regiochemistry using isomeric vinyl sulfones.
abstract: An intramolecular pyrone Diels-Alder reaction-elimination retro-Diels-Alder cascade of a vinyl sulfone was used in the synthesis of cavicularin, a molecule possessing conformational chirality. The vinyl sulfone substitution pattern allowed for regiocontrol in the Diels-Alder cascade event.
authors.affiliation: Department of Chemistry, Oregon State University, 153 Gilbert Hall, Corvallis, Oregon 97331, USA.
authors.forename: Peng
authors.initials: P
authors.lastname: Zhao
authors.forename: Christopher M
authors.initials: CM
authors.lastname: Beaudry
mesh_terms: D004988:Ethers, Cyclic / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; 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