Gleb A. Chesnokov, Julia Friedli, Francis J. Carta and Karl Gademann*,
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引用次数: 0
摘要
(-)-Bipolarolide D 是一种源自蛇床子素的雌甾烷类化合物，具有独特的四喹啉（5/5/5/5）四环骨架，并饰有多种功能。在此，我们报告了一种稳健、可扩展且高效的天然产物全合成方法，总产率为 1.8%。所开发的方法包括非对映选择性保森-汉德反应、高效的劳滕斯特劳赫环异构化、自由基环化以形成碳骨架，以及通过 1-甲基-2-丙烯基氯化镁的巴豆酰化作用安装侧链，然后进行铃木交叉偶联。
(−)-Bipolarolide D is an ophiobolin-derived sesteterpenoid with a unique tetraquinane (5/5/5/5) tetracyclic skeleton decorated with a diverse set of functionalities. Herein we report a robust, scalable, and efficient total synthesis of this natural product in 1.8% overall yield. The developed approach features a diastereoselective Pauson–Khand reaction, a highly efficient Rautenstrauch cycloisomerization, and radical cyclization to forge the carbon backbone and the installation of the side chain via crotylation with 1-methyl-2-propenylmagnesium chloride followed by Suzuki cross-coupling.
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