Total Synthesis of (+)-Coriamyrtin via a Desymmetrizing Strategy Involving a 1,3-Cyclopentanedione Moiety
Total Synthesis of (+)-Coriamyrtin via a Desymmetrizing Strategy Involving a 1,3-Cyclopentanedione Moiety
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DOI：
10.1021/acs.orglett.3c00249
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发表时间：
2023-02-28
期刊：
影响因子：
5.2
通讯作者：
Tanino，Keiji
中科院分区：
文献类型：
--
作者：
Ikeuchi，Kazutada;Haraguchi，Shota;Tanino，Keiji
我们描述了(+)-Coriamrtin的全合成，它具有高度官能化的顺式-氢化骨架，是一种广为人知的珊瑚科神经毒素。我们的合成策略包括通过分子内Aldol反应生成1，3-环戊二酮部分的去对称化策略，以及通过双环结构中环戊烷环的精细官能化形成可变霉素1，3-二环氧化物部分的高度立体选择性的构筑。
We describe the total synthesis of (+)-coriamyrtin, which bears a highly functionalizedcis-hydrindane skeleton and is a widely known neurotoxin of the Coriariaceae family. Our synthetic strategy involves the highly stereoselective construction of thecis-hydrindane skeleton via a desymmetrizing strategy involving a 1,3-cyclopentanedione moiety using an intramolecular aldol reaction and the formation of the 1,3-diepoxide moiety of coriamyrtin through the elaborate functionalization of the cyclopentane ring in the bicyclic structure.