Kelebekli Latif, Kara Yunus, Balci Metin
Department of Chemistry, Atatürk University, 25240 Erzurum, Turkey.
Carbohydr Res. 2005 Sep 5;340(12):1940-8. doi: 10.1016/j.carres.2005.05.021.
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.
已从环辛四烯出发合成了具有康杜立醇 -A、-D 和 -F 结构的双高康杜立醇衍生物。反式 -7,8 - 二溴 - 和顺式 -7,8 - 二氯双环[4.2.0]辛 -2,4 - 二烯的光氧化反应生成了双环内过氧化物。用过硫脲还原内过氧化物，随后进行乙酰化反应，得到相应的二乙酸酯。二乙酸酯经高锰酸钾氧化和环氧化反应，随后进行乙酰化反应，得到四乙酸酯。用锌粉或蒽钠除去卤化物，随后对四乙酸酯进行氨解反应，以高产率得到双高康杜立醇衍生物。
