大豆胞囊线虫中Daumone信息素的从头不对称合成及生物学分析
De Novo Asymmetric Synthesis and Biological Analysis of the Daumone Pheromones in and in the Soybean Cyst Nematode .
作者信息
Guo Haibing, La Clair James J, Masler Edward P, O'Doherty George, Xing Yalan
机构信息
School of Nuclear Technology and Chemistry & Life Science, Hubei University of Science and Technology, Xianning 437100, China.
Xenobe Research Institute, P. O. Box 3052, San Diego, CA 92163-1052, USA.
出版信息
Tetrahedron. 2016 May 5;72(18):2280-2286. doi: 10.1016/j.tet.2016.03.033. Epub 2016 Mar 16.
The asymmetric total syntheses of daumone , daumone along with 5 new analogs are described. The key steps of our approach are: the diastereoselective palladium catalyzed glycosylation reaction; the Noyori reduction of 2-acetylfuran and an ynone, which introduce the absolute stereochemistry of the sugar and aglycon portion of daumone; and an Achmatowicz rearrangement, an epoxidation and a ring opening installing the remaining asymmetry of daumone. The synthetic daumones and as well as related analogs were evaluated for dauer activity in and for effects on hatching of the related nematode . This data provides additional structure activity relationships (SAR) that further inform the study of nematode signaling.
本文描述了道莫酮的不对称全合成，以及道莫酮和5种新类似物的合成。我们方法的关键步骤包括：非对映选择性钯催化的糖基化反应；2-乙酰基呋喃和炔酮的诺伊里还原反应，该反应引入了道莫酮糖部分和苷元部分的绝对立体化学；以及阿赫马托维茨重排、环氧化和开环反应，这些反应构建了道莫酮其余的不对称性。对合成的道莫酮及其相关类似物进行了在[具体实验条件]下的滞育活性评估以及对相关线虫孵化的影响评估。这些数据提供了额外的构效关系（SAR），进一步为线虫信号传导的研究提供了信息。
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