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

doi:10.1002/chem.201304110

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

Research output: Contribution to journal › Article › peer-review

22 Citations (Scopus)

Abstract

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.

Original language	English
Pages (from-to)	1247-1251
Number of pages	5
Journal	Chemistry - A European Journal
Volume	20
Issue number	5
DOIs	https://doi.org/10.1002/chem.201304110
Publication status	Published - 2014 Jan 27
Externally published	Yes

Keywords

Chiriquitoxin
Natural products
Pummerer rearrangement
Tetrodotoxin
Total synthesis

ASJC Scopus subject areas

Catalysis
Organic Chemistry

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10.1002/chem.201304110

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abstract = "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.",

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AU - Adachi, Masaatsu

AU - Imazu, Takuya

AU - Sakakibara, Ryo

AU - Satake, Yoshiki

AU - Isobe, Minoru

AU - Nishikawa, Toshio

PY - 2014/1/27

Y1 - 2014/1/27

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AB - 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.

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KW - Natural products

KW - Pummerer rearrangement

KW - Tetrodotoxin

KW - Total synthesis

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Total synthesis of chiriquitoxin, an analogue of tetrodotoxin isolated from the skin of a dart frog

Abstract

Keywords

ASJC Scopus subject areas

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