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首页> 外文期刊>Chemistry: A European journal >The truth about false unicorn (Chamaelirium luteum): Total synthesis of 23R,24S-chiograsterol B defines the structure and stereochemistry of the major saponins from this medicinal herb
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The truth about false unicorn (Chamaelirium luteum): Total synthesis of 23R,24S-chiograsterol B defines the structure and stereochemistry of the major saponins from this medicinal herb

机译：假独角兽（Chamaelirium luteum）的真相：23R，24S-紫草甾醇B的全合成定义了这种药用草药中主要皂苷的结构和立体化学

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摘要

Chamaelirium luteum is used in traditional medicine systems and commercial botanical dietary supplements for the treatment of female reproductive health problems. Despite the wide use of this herb, only very limited phytochemical characterisation is available. Our investigation of C. luteum roots led to the isolation of two new steroidal saponins 1 and 2 that contain an unusual aglycone 3. The absolute configurations of these molecules were unable to be determined spectroscopically and thus the total synthesis of 3 was undertaken and achieved in 16 steps and 1.6 % overall yield from pregnenolone. The key step in the synthesis was the stereoselective installation of the side chain at C-17 and C-20, which employed anion-accelerated oxy-Cope methodology. The relative configuration of aglycone 3 was determined by X-ray crystallography of an advanced synthetic intermediate. The absolute configuration was based upon that of the pregnenolone-derived steroidal skeleton and determined to be 23R,24S.
机译：黄褐藻在传统医学体系和商业植物性膳食补充剂中用于治疗女性生殖健康问题。尽管这种草药得到了广泛的应用，但是只能获得非常有限的植物化学特征。我们对黄褐线虫根的研究导致分离出两个新的类固醇皂苷1和2，它们含有一个不寻常的糖苷配基3。这些分子的绝对构型无法通过光谱法确定，因此3的总合成得以实现。孕烯醇酮有16个步骤，总产率为1.6％。合成的关键步骤是在C-17和C-20侧链的立体选择性安装，该方法采用阴离子加速的oxy-Cope方法。糖苷配基3的相对构型是通过高级合成中间体的X射线晶体学测定的。绝对构型基于孕烯醇酮衍生的甾体骨架的构型，确定为23R，24S。

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