General Diastereoselective Synthetic Approach toward Isospongian Diterpenes. Synthesis of (鈭?-Marginatafuran, (鈭?-Marginatone, and (鈭?-20-Acetoxymarginatone

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• 作者：Antonio Gris ; Nuria Cabedo ; Ismael Navarro ; Ignacio de Alfonso ; Consuelo Agull贸 ; Antonio Abad-Somovilla
• 刊名：The Journal of Organic Chemistry
• 出版年：2012
• 出版时间：July 6, 2012
• 年：2012
• 卷：77
• 期：13
• 页码：5664-5680
• 全文大小：578K
• 年卷期：v.77,no.13(July 6, 2012)
• ISSN：1520-6904

文摘

This work describes a synthetic approach to the carbocyclic skeleton of isospongian diterpenes that uses the commercially available monoterpene (S)-carvone as a C-ring synthon, which is incorporated into the tetracyclic isospongian framework via a C鈫扐BC鈫扐BCD ring annulation strategy using intramolecular Diels鈥揂lder and ring-closing metathesis reactions. This approach has been successfully used to prepare both the title natural isospongians and several nonnatural oxygenated analogues. A preliminary evaluation of the inhibitory activity of the small collection of synthesized isospongians on the mammalian mitochondrial respiratory chain revealed that most were able to inhibit the integrated electron transfer chain (NADH oxidase activity) in the micromolar range.