A synthesis of (+)-saxitoxin
A synthesis of (+)-saxitoxin
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DOI：
10.1021/ja0608545
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发表时间：
2006-03-29
影响因子：
15
通讯作者：
Du Bois, J
中科院分区：
文献类型：
--
作者：
Fleming, JJ;Du Bois, J
本文报道了双胍类毒物（+）-石房蛤毒素（STX）的不对称合成。从一个N，O-缩醛起始材料通过氨基磺酸酯C-H胺化容易获得，完成的路线STX展示了oxathiazinane二氧化物杂环的多官能化胺衍生物的组装的效用。在最后的制备阶段，一个不寻常的九元环胍中间体被选择性氧化，并进行脱水环化，以提供天然产物的三环核心。获得STX和相关结构将提供独特的药理学工具的电压调节的Na+离子通道蛋白的研究。
An asymmetric synthesis of the bis-guanidinium poison, (+)-saxitoxin (STX), is described. Commencing from anN,O-acetal starting material made readily available through sulfamate ester C−H amination, the completed route to STX showcases the utility of oxathiazinane dioxide heterocycles for the assembly of polyfunctionalized amine derivatives. In the final preparative stages, an unusual nine-membered ring guanidine intermediate is oxidized selectively and made to undergo dehydrative cyclization to afford the tricyclic core of the natural product. Access to STX and related structures will provide unique pharmacological tools for the study of voltage-regulated Na+ion channel proteins.