Enantioselective total synthesis of brevetoxin A: unified strategy for the B, E, G, and J subunits.
Enantioselective total synthesis of brevetoxin A: unified strategy for the B, E, G, and J subunits.
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短尾毒素 A 的对映选择性全合成：B、E、G 和 J 亚基的统一策略。
DOI：
10.1002/chem.200900776
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发表时间：
2009
期刊：
影响因子：
--
通讯作者：
Zuccarello,JLucas
中科院分区：
文献类型：
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作者：
Crimmins,MichaelT;Ellis,JMichael;Emmitte,KyleA;Haile,PamelaA;McDougall,PatrickJ;Parrish,JonathanD;Zuccarello,JLucas
Brevetoxin A是一种十环阶梯毒素，具有5 -、6 -、7 -、8 -和9 -成员氧环，以及22个四面体立体中心。在此，我们描述了一个统一的方法来B， E， G和J环基于环闭合策略，从相应的二烯。我们实验室开发的烯醇化技术允许获得B、E和G中环醚的前体无环二烯。为合成这四个单环而开发的策略最终提供了每个环的多图数量，支持我们完成brevetoxin a的聚合合成的努力。
Brevetoxin A is a decacyclic ladder toxin that possesses 5‐, 6‐, 7‐, 8‐, and 9‐membered oxacycles, as well as 22 tetrahedral stereocenters. Herein, we describe a unified approach to the B, E, G, and J rings based upon a ring‐closing metathesis strategy from the corresponding dienes. The enolate technologies developed in our laboratory allowed access to the precursor acyclic dienes for the B, E, and G medium‐ring ethers. The strategies developed for the syntheses of these four monocycles ultimately provided multigram quantities of each of the rings, supporting our efforts toward the completion of a convergent synthesis of brevetoxin A.