Department of Chemistry, Graduate School of Science, Osaka City University, Osaka, Osaka 558-8585, Japan.
Graduate School of Agricultural Science, Tohoku University, Sendai, Miyagi 980-8572, Japan.
Org Lett. 2021 Mar 5;23(5):1703-1708. doi: 10.1021/acs.orglett.1c00125. Epub 2021 Feb 12.
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))-catalyzed cycloisomerization reaction. The concept was applied to the synthesis of 11--6,7,8-trideoxyTTX and 11--4,9-anhydro-6,7,8-trideoxyTTX, which are unnatural TTX analogues, demonstrating the validity of our new approach.
在本研究中，我们提出了一种新的合成河豚毒素（TTX）的方法，TTX 是最著名的海洋毒素之一。我们首先通过汞三氟甲磺酸（Hg(OTf)）催化的环异构化反应，以功能化的线性底物为原料，合成出环己烷核心。我们将这一概念应用于 11--6,7,8-去氧 TTX 和 11--4,9-脱水-6,7,8-去氧 TTX 的合成，这些都是非天然的 TTX 类似物，证明了我们新方法的有效性。
