Stereocontrolled Synthesis of 8,11-Dideoxytetrodotoxin,An Unnatural Analogue of Puffer Fish Toxin

Toshio Nishikawa; Daisuke Urabe; Kazumasa Yoshida; Tomoko Iwabuchi; Masanori Asai; Minoru Isobe

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Stereocontrolled Synthesis of 8,11-Dideoxytetrodotoxin,An Unnatural Analogue of Puffer Fish Toxin

机译：立体控制的8,11-双脱氧河豚毒素的合成，河豚鱼毒素的一种非天然类似物

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8,11-Dideoxytetrodotoxin,an unnatural tetrosotoxin analogue,was synthesized in a highly stereoselective manner from a common intermediate from our synthetic studies on tetrodotoxin.The key features in the synthesis were as follows:neighboring group participation of a trichloroacetamide to allow regioselective and stereoselective hydroxylation,protection of a delta-hydroxylactone as an ortho ester,and guanidine installation through the use of Boc-protected isothiourea.Global deprotection of the fully protected intermediate under acidic conditions gave 8,11-dideoxytetrodotoxin,which exhibited very weak biological activities.

机译：从我们合成的河豚毒素的普通中间体中，以高度立体选择性的方式合成了8,11-脱氧河豚毒素类似物，这是一种非天然的河豚毒素类似物。该合成的主要特征如下：三氯乙酰胺的相邻基团参与使得区域选择性和立体选择性通过使用Boc保护的异硫脲进行羟基化，保护δ-羟基内酯作为原酸酯和安装胍基化合物。在酸性条件下对完全保护的中间体进行全局脱保护，得到8,11-二脱氧河豚毒素，其生物活性非常弱。

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来源
《Chemistry: A European journal》 |2004年第2期|共11页
作者
Toshio Nishikawa; Daisuke Urabe; Kazumasa Yoshida; Tomoko Iwabuchi; Masanori Asai; Minoru Isobe;
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正文语种 eng
中图分类化学;
关键词
asymmetric synthesis; ion channels; natural products; tetrodotoxin; total synthesis;

机译：不对称合成离子通道天然产物河豚毒素全合成;

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1. Stereocontrolled Synthesis of 8,11-Dideoxytetrodotoxin,An Unnatural Analogue of Puffer Fish Toxin [J] . Toshio Nishikawa, Daisuke Urabe, Kazumasa Yoshida, Chemistry: A European journal . 2004,第2期

机译：立体控制的8,11-双脱氧河豚毒素的合成，河豚鱼毒素的一种非天然类似物
2. Rapid screening and multi-toxin profile confirmation of tetrodotoxins and analogues in human body fluids derived from a puffer fish poisoning incident in New Caledonia [J] . Rambla-Alegre Maria, Leonardo Sandra, Barguil Yann, Food and Chemical Toxicology: An International Journal Published for the British Industrial Biological Research . 2018,第期

机译：快速筛选和多毒素谱系源于新喀里多尼亚河豚鱼中毒事件的人体流体中的四抗毒素和类似物
3. Multifunctionality of the N-Trichloroacetyl Group Developed in the Synthesis of Tetrodotoxin, a Puffer Fish Toxin [J] . Nishikawa Toshio, Urabe Daisuke, Adachi Masaatsu, Synlett . 2015,第14期

机译：河豚毒素河豚毒素的合成中开发的N-三氯乙酰基的多功能。
4. Oxathiaphospholane method of the stereocontrolled synthesis of phosphorothioate analogues of oligonucleotides [C] . A. Okruszek NATO advanced research workshop on RNA biochemistry and biotechnology . 1999

机译：寡核苷酸磷硫代磷酸磷酸酯基数的恶毒磷酸磷烷磷膦法
5. A comprehensive study of the Hong Kong puffer fishes and their toxins. [D] . Yu, Chun Fai. 2003

机译：对香港河豚鱼及其毒素的综合研究。
6. A Novel and Efficient Synthesis of NN-Dialkylaminoisopropyl- and O-alkylisopropyl-2-(1-alkyl-2-oxopropylidene)phosphono- hydrazido Oximes - Potential Marine Fish Toxin Analogues. Part 1 [O] . Rajesh Kumar, Arvind K. Gupta, Mahabir P. Kaushik 2007

机译：NN-二烷基氨基异丙基和O-烷基异丙基-2-（1-烷基-2-氧代亚丙基）膦酰肼基肟的新型有效合成-潜在的海水鱼类毒素类似物。第1部分
7. Rapid screening and multi-toxin profile confirmation of tetrodotoxins and analogues in human body fluids derived from a puffer fish poisoning incident in New Caledonia [O] . Maria Rambla-Alegre, Sandra Leonardo, Yann Barguil, 2018

机译：快速筛选和多毒素型材对北·喀尔甸河豚鱼中毒事件衍生的人体液体中的四毒素和类似物
8. Biological and Fisheries Data on Northern Puffer, 'Sphoeroides maculatus' (Bloch and Schneider) [R] . Sibunka, J. D. , Pacheco, A. L. 1981

机译：北方河豚生物和渔业数据'sphoeroides maculatus'（Bloch和schneider）

Stereocontrolled Synthesis of 8,11-Dideoxytetrodotoxin,An Unnatural Analogue of Puffer Fish Toxin

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