Synthesis of the I-K Fused Polyether Array of CTX3C and Related Ciguatoxins by Use of a Gold-Catalyzed Cyclization Reaction
Synthesis of the I-K Fused Polyether Array of CTX3C and Related Ciguatoxins by Use of a Gold-Catalyzed Cyclization Reaction
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DOI：
10.1021/acs.orglett.3c03782
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发表时间：
2024-01-18
期刊：
影响因子：
5.2
通讯作者：
Clark，J. Stephen
中科院分区：
文献类型：
--
作者：
Chintalapudi，Venkaiah;Wilson，Claire;Clark，J. Stephen
从四氢吡喃醇衍生的简单手性池合成了雪卡毒素CTX 3C的I-K片段（C31-C49）。利用金催化的γ′-羟基炔酮的环化反应，在温和条件下实现了K环的有效闭合。得到的乙烯基酯已被精心制作，以得到一个完整的三环片段轴承的LM螺环缩醛部分的目标组件所需的二甲基取代的侧链。
The I–K fragment (C31–C49) of the ciguatoxin CTX3C has been synthesized from a simple chiral pool derived tetrahydropyranyl alcohol. An efficient gold-catalyzed cyclization reaction of a γ′-hydroxy ynone has been used to accomplish efficient closure of ring K under mild conditions. The resulting vinylogous ester has been elaborated to give a complete tricyclic fragment bearing the dimethyl-substituted side chain required for assembly of the LM spirocyclic acetal portion of the target.