Stereospecific synthesis of a new class of compounds: bis-homoconduritol-A, -D, and -F.
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.
Kelebekli
Latif
L
Department of Chemistry, Atatürk University, 25240 Erzurum, Turkey.
Kara
Yunus
Y
Balci
Metin
M
D001643:Bridged Bicyclo Compounds / Q000138:chemical synthesis*; D006844:Hydrocarbons, Cyclic / Q000737:chemistry; D013237:Stereoisomerism
D001643:Bridged Bicyclo Compounds; D006844:Hydrocarbons, Cyclic