title: A Concise and Convenient Synthesis of DL-proto-Quercitol and DL-gala-Quercitol via Ene Reaction of Singlet Oxygen Combined with [2 + 4] Cycloaddition to Cyclohexadiene.
abstract: Photooxygenation of 1,4-cyclohexadiene afforded hydroperoxy endoperoxides 3 and 4 in a ratio of 88:12. Reduction of 3 with LiAlH(4) or thiourea followed by acetylation of the hydroxyl group and KMnO(4) oxidation of the double bond gave proto-quercitol 10b. Application of the same reaction sequences to 4 resulted in the formation of gala-quercitol 14. Quercitols were easily obtained by ammonolysis of acetate derivatives in MeOH. The outcome of dihydroxylation reactions were supported by conformational analysis.
authors.affiliation: Department of Chemistry, Faculty of Arts and Sciences, Atatürk University, 25240-Erzurum, Turkey.
authors.forename: Emine
authors.initials: E
authors.lastname: Salamci
authors.forename: Hasan
authors.initials: H
authors.lastname: Seçen
authors.forename: Yasar
authors.initials: Y
authors.lastname: Sütbeyaz
authors.forename: Metin
authors.initials: M
authors.lastname: Balci