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.
Emerging Area
The role of chemical synthesis in structure elucidation of oxasqualenoids
*Corresponding authors
aDepartment of
Chemistry, Graduate School of Science, Osaka City University,
Sumiyoshi-ku, Japan
E-mail: morimoto@sci.osaka-cu.ac.jp
Fax: +81 6 6605 2522
Tel: +81 6 6605 3141
E-mail: morimoto@sci.osaka-cu.ac.jp
Fax: +81 6 6605 2522
Tel: +81 6 6605 3141
Org. Biomol. Chem., 2008,6, 1709-1719
DOI: 10.1039/B801126E
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