title: Functionalized 3(2H)-furanones via photooxygenation of (β-keto)-2-substituted furans: application to the biomimetic synthesis of merrekentrone C.
abstract: Photooxygenation of (β-keto)-2-substituted furans leads, in a one pot operation, to functionalized 3(2H)-furanones with good to excellent yields. This methodology was applied as a key-step to the concise and biomimetic synthesis of the sesquiterpene merrekentrone C. The precursor to merrekentrone C, keto difuran, was synthesized using a cross coupling of α-iodo-3-acetylfuran with an alkenyl furan under Fenton-type conditions.
authors.affiliation: Department of Chemistry, University of Crete, Voutes, Iraklion, Greece.
authors.forename: Charis
authors.initials: C
authors.lastname: Gryparis
authors.forename: Ioannis N
authors.initials: IN
authors.lastname: Lykakis
authors.forename: Christina
authors.initials: C
authors.lastname: Efe
authors.forename: Ioannis-Panayotis
authors.initials: IP
authors.lastname: Zaravinos
authors.forename: Theonymphi
authors.initials: T
authors.lastname: Vidali
authors.forename: Eugenia
authors.initials: E
authors.lastname: Kladou
authors.forename: Manolis
authors.initials: M
authors.lastname: Stratakis
mesh_terms: D001688:Biological Products / Q000138:chemical synthesis*; D032701:Biomimetics / Q000379:methods*; D027722:Convolvulaceae / Q000737:chemistry*; D005663:Furans / Q000138:chemical synthesis / Q000737:chemistry*; D012717:Sesquiterpenes / Q000138:chemical synthesis*
chemical_list: D001688:Biological Products; D005663:Furans; D012717:Sesquiterpenes; C568204:merrekentrone C