Salacinol结构类似简化物的设计与合成(英文)

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。

Design and synthesis of a simplified analogue of salacinol

To investigate a key strategy of the total synthesis of salacinol. Methods: A simplified analogue of salacinol (1),1-(3-sulfooxypropyl)tetrahydrothiophenium inner salt (2) was designed and synthesized by a coupling reaction between tetrahydrothiophene (THT) and 3-iodopropanol (3-IPA) followed by the esterification of the resulting sulfonium with sulfur trioxide pyridine complex (SO3*Py). Replacement of the alkylating reagent (3-IPA) of THT led to the predominate formation of a undesirable cyclic compound,2,2-dioxo-1,3,2-dioxathiane (7). Resutls:This model experiments indicated that the tandem synthetic process leading to the sulfonium sulfate 2 could be applied for the total synthesis of salacinol (1) as an alternative method.