Morimoto Yoshiki
Department of Chemistry, Graduate School of Science, Osaka City University, Sumiyoshi-ku, Osaka 558-8585, Japan.
Org Biomol Chem. 2008 May 21;6(10):1709-19. doi: 10.1039/b801126e. Epub 2008 Mar 17.
Recently, highly oxidized and structurally diverse triterpene polyethers, which are thought to be biogenetically squalene-derived natural products (oxasqualenoids), have been isolated from both marine and terrestrial organisms. However, it is often difficult to determine their stereostructures even by the current, highly advanced spectroscopic methods, especially in acyclic systems including stereogenic quaternary carbon centers. In such cases, it is effective to predict and synthesize the possible stereostructures. Herein, we report total assignments of the previously incomplete stereostructures of an epoxy tri-THF diol, intricatetraol and enshuol, members of the oxasqualenoids, through the first asymmetric total syntheses of the natural products, the configurations of which are difficult to determine by other means. Since this article is basically written as a communication without detailed experimental procedures and spectroscopic data, original papers with full data should follow.
最近，高度氧化且结构多样的三萜聚醚类化合物被从海洋生物和陆地生物中分离出来，这类化合物被认为是生源合成的源自角鲨烯的天然产物（氧化角鲨烯类化合物）。然而，即便使用当前高度先进的光谱方法，通常也难以确定它们的立体结构，尤其是在包含手性季碳中心的无环体系中。在这种情况下，预测并合成可能的立体结构是有效的。在此，我们通过首次不对称全合成这些天然产物，报道了氧化角鲨烯类化合物环氧三 - 四氢呋喃二醇、复杂四醇和远州醇之前不完整的立体结构的完全归属，这些天然产物的构型难以通过其他方法确定。由于本文基本上是作为一篇通讯撰写的，没有详细的实验步骤和光谱数据，完整数据的原始论文应随后发表。
