title: Stereospecific synthesis of a new class of compounds: bis-homoconduritol-A, -D, and -F.
abstract: Bis-homoconduritol derivatives with conduritol-A, -D, and -F structures have been synthesized starting from cyclooctatetraene. The photooxygenation of trans-7,8-dibromo- and cis-7,8-dichlorobicyclo[4.2.0]octa-2,4-dienes afforded the bicyclic endoperoxides. Reduction of the endoperoxides with thiourea followed by acetylation gave the corresponding diacetates. The KMnO(4) oxidation and epoxidation of the diacetates followed by acetylation gave the tetraacetates. Removal of the halides either with zinc-dust or Na-anthracene followed by the ammonolysis of tetraacetates afforded the bis-homoconduritol derivatives in high yield.
authors: Department of Chemistry, Atatürk University, 25240 Erzurum, Turkey.
authors: Latif
authors: L
authors: Kelebekli
authors: Yunus
authors: Y
authors: Kara
authors: Metin
authors: M
authors: Balci
mesh_terms: D001643:Bridged Bicyclo Compounds / Q000138:chemical synthesis*; D006844:Hydrocarbons, Cyclic / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D001643:Bridged Bicyclo Compounds; D006844:Hydrocarbons, Cyclic