Anodic coupling reactions: probing the stereochemistry of tetrahydrofuran formation. A short, convenient synthesis of linalool oxide.
[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.
Duan
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S
Department of Chemistry, Washington University, St. Louis, Missouri 63130, USA.
Moeller
K D
KD
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
D000080462:Acyclic Monoterpenes; D005663:Furans; D039821:Monoterpenes; D013729:Terpenes; C018674:tetrahydrofuran; C018584:linalool