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目的:探索Salacinol全合成的基本步骤。方法:根据Salacinol的结构组成,设计了其结构类似简化物1-(3-磺氧丙基)四氢噻吩锍盐(2)。以四氢噻吩和3-碘基丙醇为原料,经偶合反应和三氧化硫吡啶的酯化制得化合物2。当在相同的条件下以3-碘基丙醇硫酸酯钠替代3-碘基丙醇为烷化剂时,其主要产物经确证为3-碘基丙醇硫酸酯钠的分子内环化物1,4-丙二醇硫酸内酯(7)。结果:上述模拟实验结果提示,通过两步反应制得化合物2的方法可能为Salacinol的全合成提供一种新的途径。
Objective: To explore the basic steps of total synthesis of Salacinol. Methods: According to the structure and composition of Salacinol, 1- (3-sulfoxypropyl) tetrahydrothiophenium sulfonium salt (2) with similar structure was designed. With tetrahydrothiophene and 3 - iodopropanol as raw materials, the coupling reaction and sulfur trioxide pyridine esterification to prepare compound 2. When sodium 3-iodopropanol sulfate was used instead of 3-iodopropanol as the alkylating agent under the same conditions, the main product thereof was confirmed to be the intramolecular cyclized product of sodium 3-iodopropanol sulfate sodium 1 , 4-propanediol sultone (7). Results: The results of the above simulation suggest that the preparation of compound 2 by two-step reaction may provide a new way for the total synthesis of Salacinol.