title: Scope and limitations of the photooxidations of 2-(α-hydroxyalkyl)furans: synthesis of 2-hydroxy-exo-brevicomin.
abstract: Photooxygenation of 2-(α-hydroxyalkyl)furans at 5 °C in MeOH followed by in situ reduction affords, in one synthetic operation, 6-hydroxy-3(2H)-pyranones and/or 5-hydroxy-2(5H)-furanones. The relative ratio of the final products is highly dependent on the substitution of the starting furan substrate. Photooxygenation of 2-(α,β-dihydroxyalkyl)furans followed by in situ reduction and ketalization with acid rapidly provides the 6,8-dioxabicyclo[3.2.1]oct-3-en-2-one framework. This new methodology was successfully applied to the synthesis of 2-hydroxy-exo-brevicomin.
authors.affiliation: Department of Chemistry, University of Crete, Iraklion, Crete, Greece.
authors.forename: Dimitris
authors.initials: D
authors.lastname: Noutsias
authors.forename: Antonia
authors.initials: A
authors.lastname: Kouridaki
authors.forename: Georgios
authors.initials: G
authors.lastname: Vassilikogiannakis