Evolution of a practical total synthesis of ciguatoxin CTX3C.
Evolution of a practical total synthesis of ciguatoxin CTX3C.
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DOI：
10.1021/ar0301577
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发表时间：
2004-10
影响因子：
18.3
通讯作者：
M. Inoue;M. Hirama*
中科院分区：
文献类型：
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作者：
M. Inoue;M. Hirama*
在亚热带和热带地区，每年有2万多人因雪卡毒海鲜中毒而受害。由于鱼类体内的雪卡毒素含量极低，以致难以进行分离、详细的生物学研究，以及制备抗雪卡毒素抗体以检测这些毒素。雪卡毒素由12个六元至九元的反式稠合多环醚组成，并且在一端包括一个连接的五元环醚。雪卡毒素的大分子结构（长度为3 nm）和复杂的分子结构阻碍了化学家完成其全合成。2001年，我们首次实现了雪卡毒素CTX 3C的全合成。从那时起，联合收割机结合片段的方案在整体立体选择性、效率和实用性方面有了显著的改进。在本报告中，我们描述了最近发展的用于CTX 3C全合成的方法。
More than 20 000 people suffer annually from ciguatera seafood poisoning in subtropical and tropical regions. The extremely low content of the causative neurotoxins, designated as ciguatoxins, in fish has hampered their isolation, detailed biological study, and preparation of anti-ciguatoxin antibodies for detecting these toxins. Ciguatoxins consist of 12 trans-fused polycyclic ethers, ranging from six- to nine-membered, and include a spirally attached five-membered cyclic ether at one end. The large (3 nm in length) and complicated molecular structure of ciguatoxins has impeded chemists from completing their total synthesis. In 2001, we achieved the first total synthesis of ciguatoxin CTX3C by assembly of four structural fragments. Since then, protocols to combine the fragments have significantly improved in terms of overall stereoselectivity, efficiency, and practicality. In this Account, we describe recently evolved methodologies for the total synthesis of CTX3C.