Anodic Coupling Reactions:  Probing the Stereochemistry of Tetrahydrofuran Formation. A Short, Convenient Synthesis of Linalool Oxide

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.