Tetrodotoxin Framework Construction from Linear Substrates Utilizing a Hg(OTf)2-Catalyzed Cycloisomerization Reaction: Synthesis of the Unnatural Analogue 11-nor-6,7,8-Trideoxytetrodotoxin,Organic Letters

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Tetrodotoxin Framework Construction from Linear Substrates Utilizing a Hg(OTf)2-Catalyzed Cycloisomerization Reaction: Synthesis of the Unnatural Analogue 11-nor-6,7,8-Trideoxytetrodotoxin
Organic Letters ( IF 4.9 ) Pub Date : 2021-02-12 , DOI: 10.1021/acs.orglett.1c00125
Keisuke Nishikawa ₁ , Takayuki Noguchi ₁ , Seiho Kikuchi ₁ , Takahiro Maruyama ₁ , Yusuke Araki ₁ , Mari Yotsu-Yamashita ₂ , Yoshiki Morimoto ₁

Affiliation

In this contribution, we propose a new synthetic approach to tetrodotoxin (TTX), one of the most famous marine toxins that, after first preparing a functionalized linear substrate, forms a cyclohexane core from the substrate utilizing our mercuric triflate (Hg(OTf)₂)-catalyzed cycloisomerization reaction. The concept was applied to the synthesis of 11-nor-6,7,8-trideoxyTTX and 11-nor-4,9-anhydro-6,7,8-trideoxyTTX, which are unnatural TTX analogues, demonstrating the validity of our new approach.

中文翻译：

河豚毒素构建框架从线性底物利用（OTF）汞柱₂ -催化的反应环异构：非天然类似物的11-也不-6,7,8- Trideoxytetrodotoxin

在这项贡献中，我们提出了一种新的合成河豚毒素（TTX）的方法，河豚毒素是最著名的海洋毒素之一，在首先制备功能化线性底物后，利用我们的三氟甲磺酸汞（Hg（OTf）₂）催化的环异构化反应。该概念被用于合成11-或-6,7,8-三苯氧基TTX和11-或-4,9-脱水-6,7,8-三苯氧基TTX，它们是非天然的TTX类似物，证明了我们新产品的有效性方法。

更新日期：2021-03-05

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