Stereoselective total syntheses of three Lycopodium alkaloids, (-)-magellanine, (+)-magellaninone, and (+)-paniculatine, based on two Pauson-Khand reactions
Stereoselective total syntheses of three Lycopodium alkaloids, (-)-magellanine, (+)-magellaninone, and (+)-paniculatine, based on two Pauson-Khand reactions
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DOI：
10.1021/jo702136b
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发表时间：
2007-12-21
影响因子：
3.6
通讯作者：
Mukai, Chisato
中科院分区：
文献类型：
--
作者：
Kozaka, Takashi;Miyakoshi, Naoki;Mukai, Chisato
以L酒石酸二乙酯为原料，立体选择性地合成了(-)-麦哲伦、(+)-麦哲罗酮和(+)-酒石酸二乙酯。这些合成的关键步骤包括两个烯炔的分子内Pauson-Khandd反应：第一个Pauson-Khandd反应以高度立体选择性的方式构建了双环[4.3.0]碳骨架，相应的生物碱的A和B环，而第二个Pauson-Khandd反应立体选择性地生成了双环[3.3.0]骨架，它可以转化为目标天然产物的C环和D环。
The total syntheses of (-)-magellanine, (+)-magellaninone, and (+)-paniculatine were completed from diethyl L-tartrate via the common intermediate in a stereoselective manner. The crucial steps in these syntheses involved two intramolecular Pauson-Khand reactions of enynes: the first Pauson-Khand reaction constructed the bicyclo[4.3.0] carbon framework, the corresponding A and B rings of these alkaloids in a highly stereoselective manner, whereas the second Pauson-Khand reaction stereoselectively produced the bicyclo [3.3.0] skeleton, which could be converted into the C and D rings of the target natural products.