Total Synthesis of Chiriquitoxin, an Analogue of Tetrodotoxin Isolated from the Skin of a Dart Frog

Masaatsu Adachi; Takuya Imazu; Ryo Sakakibara; Yoshiki Satake; Minoru Isobe; Toshio Nishikawa

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Total Synthesis of Chiriquitoxin, an Analogue of Tetrodotoxin Isolated from the Skin of a Dart Frog

机译：从箭毒蛙皮中分离出河豚毒素类似物Chiriquitoxin的全合成。

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The first total synthesis of chiriquitoxin, the most structurally complex analogue of tetrodotoxin isolated from a Costa Rican dart frog, has been accomplished from a newly designed intermediate for a variety of tetrodotoxin derivatives. The synthesis includes the third total synthesis of tetrodotoxin in this laboratory, and its intermediate was transformed into chiriquitoxin by a stereocontrolled aldol reaction with a d-camphor-derived lactone for installation of the unique side chain, and a new deprotection of methylthiomethyl (MTM) ether by using a Pummerer rearrangement.

机译：从一种新设计的用于多种河豚毒素衍生物的中间体可以完成手性鸟毒素的最全面的首次合成，该方法是从哥斯达黎加箭蛙身上分离的河豚毒素的结构最复杂的类似物。该合成过程是河豚毒素的第三次总合成，其中间体通过与d-樟脑胶衍生的内酯的立体控制的醛醇缩合反应转变成手性毒素，以安装独特的侧链，以及新的甲基硫甲基脱保护（MTM）醚通过使用Pummerer重排。

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来源
《Chemistry: A European journal》 |2014年第5期|共5页
作者
Masaatsu Adachi; Takuya Imazu; Ryo Sakakibara; Yoshiki Satake; Minoru Isobe; Toshio Nishikawa;
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正文语种 eng
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关键词
chiriquitoxin; natural products; Pummerer rearrangement; tetrodotoxin; total synthesis;

机译：手淫毒素;天然产物;Pummerer重排;河豚毒素;总合成;

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1. Total Synthesis of Chiriquitoxin, an Analogue of Tetrodotoxin Isolated from the Skin of a Dart Frog [J] . Masaatsu Adachi, Takuya Imazu, Ryo Sakakibara, Chemistry: A European journal . 2014,第5期

机译：从箭毒蛙皮中分离出河豚毒素类似物Chiriquitoxin的全合成。
2. Effect of amiloride and some of its analogues of cation transport in isolated frog skin and thin lipid membranes. [J] . D J Benos, S A Simon, L J Mandel, The Journal of general physiology . 1976,第1期

机译：阿米洛利及其阳离子类似物在离体的蛙皮和薄脂膜中的作用。
3. Total synthesis of 275A lehmizidine frog skin alkaloid (or of its enantiomer) [J] . Lesma G., Sacchetti A., Silvani A. Tetrahedron, Asymmetry: The International Journal for Repid Publication on all Aspects of Asymmetry in Orgainc, Inorganic, Organometallic, Physical and Bio-Organic Chemistry . 2010,第19期

机译：275A来甲基联苯胺蛙皮生物碱（或其对映体）的全合成
4. Galanin and its analogues:synthesis and biological activity in rat isolated gastric smooth muscles [C] . Jaroslaw Ruczynski, Zdzislaw Konstanski, Roman Korolkiewicz, European Peptide Symposium . 2002

机译：环肽及其类似物：大鼠分离胃平滑肌的合成和生物活性
5. The total synthesis of biologically active C-glycoside natural products: 1) Total synthesis of (-)-centrolobine 2) Total synthesis of (-)-varitriol and analogues 3) Progress towards the total synthesis of polyrhacatide A. [D] . Clemens, Ryan Thomas. 2009

机译：具有生物活性的C-糖苷天然产物的总合成：1）（-）-中心叶绿素的总合成2）（-）-曲柄三醇和类似物的总合成3）合成多杀菌素A的进展。
6. Effect of amiloride and some of its analogues of cation transport in isolated frog skin and thin lipid membranes [O] . 1976

机译：阿米洛利及其阳离子类似物在离体蛙皮和脂膜中的作用
7. Effect of amiloride and some of its analogues of cation transport in isolated frog skin and thin lipid membranes [O] . 1976

机译：阿米洛利及其阳离子类似物在离体蛙皮和脂膜中的作用

Total Synthesis of Chiriquitoxin, an Analogue of Tetrodotoxin Isolated from the Skin of a Dart Frog

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