title: Anodic coupling reactions: probing the stereochemistry of tetrahydrofuran formation. A short, convenient synthesis of linalool oxide.
abstract: [reaction: see text]. Intramolecular coupling reactions between enol ether radical cations and oxygen nucleophiles are primarily governed by stereoelectronics. By taking advantage of this observation, a tetrahydrofuran building block for use in constructing (+)-linalool oxide and rotundisine has been synthesized in four steps from a commercially available starting material. The synthesis of (+)-linalool oxide has been completed.
authors.affiliation: Department of Chemistry, Washington University, St. Louis, Missouri 63130, USA.
authors.forename: S
authors.initials: S
authors.lastname: Duan
authors.forename: K D
authors.initials: KD
authors.lastname: Moeller
mesh_terms: D000080462:Acyclic Monoterpenes; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D039821:Monoterpenes; D013237:Stereoisomerism; D013729:Terpenes / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000080462:Acyclic Monoterpenes; D005663:Furans; D039821:Monoterpenes; D013729:Terpenes; C018674:tetrahydrofuran; C018584:linalool