title: Synthesis of cyclobutane lignansviaan organic single electron oxidant-electron relay system.
abstract: A direct method to synthesize lignan cyclobutanes and analogsviaphotoinduced electron transfer is presented. A variety of oxygenated alkenes are employed to furnish terminal or substituted cyclobutane adducts with complete regiocontrol, yielding cycloadducts withtransstereochemistry. Key to minimizing competing cycloreversion is the inclusion of an aromatic electron relay (ER). This method has been adapted to the synthesis of the natural products magnosalin and pellucidin A.
authors.affiliation: Department of Chemistry, University of North Carolina at Chapel Hill, Chapel Hill, NC 27599-3290, USA.
authors.forename: Michelle
authors.initials: M
authors.lastname: Riener
authors.affiliation: Department of Chemistry, University of North Carolina at Chapel Hill, Chapel Hill, NC 27599-3290, USA.
authors.forename: David A
authors.initials: DA
authors.lastname: Nicewicz