Total Synthesis of Antiausterity Agent (±)-Uvaridacol L by Regioselective Axial Diacylation of a myo-Inositol Orthoester
Total Synthesis of Antiausterity Agent (±)-Uvaridacol L by Regioselective Axial Diacylation of a myo-Inositol Orthoester
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DOI：
10.1021/acs.orglett.1c00079
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发表时间：
2021-02-17
期刊：
影响因子：
5.2
通讯作者：
Okuda, Kensuke
中科院分区：
文献类型：
--
作者：
Takagi, Akira;Usuguchi, Kazuki;Okuda, Kensuke
抗紧缩天然产物(+/-)-uvaridacol L是首次由肌醇通过七个步骤合成的。该合成的关键反应是使用催化量的四丁基氟化铵 (TBAF) 实现肌醇原甲酸酯的轴向选择性二苯甲酰化。还在营养缺乏条件下评估了外消旋 uvaridacol L 对能够适应营养缺乏的癌细胞系的优先细胞毒性。还进行了形态学评价。
The antiausterity natural product (+/-)-uvaridacol L was synthesized for the first time in seven steps from myo-inositol. The key reaction of this synthesis, axial selective dibenzoylation of myo-inositol orthoformate, was achieved using a catalytic amount of tetrabutylammonium fluoride (TBAF). The preferential cytotoxicity of racemic uvaridacol L against cancer cell lines able to adapt to nutrient deprivation was also evaluated under nutrient deprived conditions. Morphological evaluation was also carried out.