Adachi Masaatsu, Imazu Takuya, Sakakibara Ryo, Satake Yoshiki, Isobe Minoru, Nishikawa Toshio
Laboratory of Organic Chemistry, Graduate School of Bioagricultural Sciences, Nagoya University, Chikusa, Nagoya 464-8601 (Japan), Fax: (+81) 52-789-4111.
Chemistry. 2014 Jan 27;20(5):1247-51. doi: 10.1002/chem.201304110.
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.
从哥斯达黎加箭毒蛙中分离出的结构最复杂的河豚毒素类似物奇里基毒素的首次全合成，是通过一种新设计的中间体完成的，该中间体可用于多种河豚毒素衍生物的合成。该合成包括本实验室的第三次河豚毒素全合成，其中间体通过与D-樟脑衍生的内酯进行立体控制的羟醛反应，以安装独特的侧链，并通过普默勒重排对甲硫基甲基（MTM）醚进行新的脱保护，从而转化为奇里基毒素。
