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首页> 外文期刊>Chemistry: A European journal >Total Synthesis of the Antitumor Acetogenin Mosin B: Desymmetrization Approach to the Sterodivergent Synthesis of threo/trans/erythro-Type Acetogenins
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Total Synthesis of the Antitumor Acetogenin Mosin B: Desymmetrization Approach to the Sterodivergent Synthesis of threo/trans/erythro-Type Acetogenins

机译：抗肿瘤产乙酸原蛋白Mosin B的全合成：苏氨酸/反式/赤型产乙酸原蛋白立体异构合成的不对称化方法。

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摘要

A total synthesis of the threo/trans/erythro-type acetogenin mosin B and one of its diastereomers has been achieved. The carbon skeleton is assembled in a convergent fashion from two segments (a THF ring segment and a gamma-lactone segment) through the Nozaki-Hiyama-Kishi reaction. The THF ring segment was stereoselectively constructed by a stereodivergent synthesis starting from a common intermediate (4-cyclohexene-1,2-diol) based on a desymmetrization strategy. The gamma-lactone segment was synthesized by coupling a triflate and a chiral alpha-sulfenyl gamma-lactone. By virtue of these synthetic results, we suggest that the absolute configuration of natural mosin B is 1a. Antiproliferative effects of 1a and 1b were also investigated.
机译：苏氨酸/反式/赤型产乙酸原蛋白mosin B及其非对映异构体之一的全合成。通过野崎-山山-纪史反应，由两个链段（THF环链段和γ-内酯链段）以汇聚方式组装碳骨架。 THF环链段是基于不对称化策略，从常见的中间体（4-环己烯-1,2-二醇）通过立体发散合成立体选择性地构建的。 γ-内酯链段是通过将三氟甲磺酸酯和手性α-亚磺酰基γ-内酯偶联而合成的。根据这些合成结果，我们建议天然mosin B的绝对构型为1a。还研究了1a和1b的抗增殖作用。

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