Synthetic Strategies toward Natural Products Containing Contiguous Stereogenic Quaternary Carbon Atoms.
Synthetic Strategies toward Natural Products Containing Contiguous Stereogenic Quaternary Carbon Atoms.
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DOI：
10.1002/anie.201507549
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发表时间：
2016-03-18
期刊：
影响因子：
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通讯作者：
Overman LE
中科院分区：
文献类型：
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作者：
Büschleb M;Dorich S;Hanessian S;Tao D;Schenthal KB;Overman LE
综述了复杂结构中含有两个或多个连续立体生成的四元碳原子的复杂天然产物的全合成策略，并列举了12个具有代表性的例子。重点放在创建四元碳立体中心的方法上，包括来自不同基团的同一天然产物的合成，从而展示了思维的多样性和个人的创造力。辅助资料部分提供了选定的天然产物的概要，其中包含两个或更多连续的立体生成的四元碳原子及其全部或部分合成中的关键反应。虽然生物合成很容易通过自然界的进化机制以及其他各种酶过程来完成，但通过全合成在天然产品中加入多个季碳中心是合成化学家几十年来面临的最艰巨的挑战之一。在过去50年或更长的时间里，这一领域取得了惊人的进步，1953年Dauben首次合成胡枝子，Maimone在2015年合成金丝桃素就证明了这一点。在这篇综述中，我们重点介绍了不同研究小组对一组选定的含有两个或更多连续的季碳原子的天然产物的立体控制全合成所使用的策略
Strategies for the total synthesis of complex natural products that contain two or more contiguous stereogenic quarternary carbon atoms in their intricate structures are reviewed with twelve representative examples. Emphasis has been put on the methods to create quarternary carbon stereocenters, including syntheses of the same natural product from different groups, thereby showcasing diversity of thought and individual creativity. A compendium of selected natural products containing two or more contiguous stereogenic quarternary carbon atoms and key reactions in their total or partial syntheses is provided in the Supporting Information section. While biosynthetically easily accomplished by Nature’s evolutionary machinery with an arsenal of enzymatic processes among others, the incorporation of multiple quaternary carbon centers in natural products by total synthesis is one of the most daunting challenges that have faced synthetic chemists for decades. The period spanning the last 50 or more years has seen phenomenal progress in this area as evidenced by the first synthesis of thujopsene by Dauben in 1953, and the last synthesis of hyperforin by Maimone in 2015. In this review we highlight strategies used by different research groups toward the stereocontrolled total synthesis of a selected group of natural products that contain two or more contiguous quaternary carbon atoms