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

研究成果: Article査読

22 被引用数 (Scopus)

抄録

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.

本文言語English
ページ(範囲)1247-1251
ページ数5
ジャーナルChemistry - A European Journal
20
5
DOI
出版ステータスPublished - 2014 1月 27
外部発表はい

ASJC Scopus subject areas

  • 触媒
  • 有機化学

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