Department of Chemistry, Faculty of Sciences and Arts, Ordu University, 52200, Ordu, Turkey.
Department of Chemistry, Faculty of Sciences, Ataturk University, 25240, Erzurum, Turkey.
Carbohydr Res. 2022 Sep;519:108611. doi: 10.1016/j.carres.2022.108611. Epub 2022 Jun 11.
Starting from cyclooctatetraene, bis-homoconduritols with cis-inositol and allo-inositol (or bicyclo[4.2.0]octane motif) structures were synthesized. Photooxygenation of trans-7,8-dibromo-bicyclo[4.2.0]octa-2,4-diene allowed the preparation of tricyclic endoperoxide. The compound diacetate was obtained by reduction of endoperoxide with thiourea followed by acetylation reaction. Removal of halides with zinc dust in acetic acid yielded the dien-diacetate, a key compound of the designed molecules. OsO oxidation of diendiacetate followed by acetylation gave the corresponding hexaacetates. Finally, the novel desired bis-homoinositols were obtained in high yield by the ammonolysis of acetate groups. The structures of all synthesized compounds were characterized by spectroscopic methods.
从环辛四烯出发，合成了具有顺式肌醇和别肌醇（或双环[4.2.0]辛烷结构）结构的双-同型甘露糖醇。反式-7,8-二溴双环[4.2.0]辛-2,4-二烯的光氧化反应允许制备三环内过氧化物。过氧化物用硫脲还原，然后进行乙酰化反应，得到化合物二乙酸酯。在乙酸中用锌粉除去卤化物，得到双烯二乙酸酯，这是设计分子的关键化合物。二烯二乙酸酯的 OsO 氧化反应，然后进行乙酰化反应，得到相应的六乙酸酯。最后，通过乙酸盐基团的氨解反应，以高产率得到了新型所需的双同型肌醇。所有合成化合物的结构均通过光谱方法进行了表征。
