Convergent synthesis of the HIJKLM ring fragment of ciguatoxin CTX3C

Hisatoshi Uehara; Tohru Oishi; Masayuki Inoue; Mitsuru Shoji; Yoko Nagumo; Masashi Kosaka; Jean Yves Le Brazidec; Masahiro Hirama

doi:10.1016/S0040-4020(02)00660-9

Convergent synthesis of the HIJKLM ring fragment of ciguatoxin CTX3C

Hisatoshi Uehara, Tohru Oishi, Masayuki Inoue, Mitsuru Shoji, Yoko Nagumo, Masashi Kosaka, Jean Yves Le Brazidec, Masahiro Hirama

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

56 Citations (Scopus)

Abstract

Ciguatoxin CTX3C is a representative congener of the ciguatoxins, which are known to be the principal causative agents of ciguatera food poisoning. The structure of CTX3C spans more than 3nm and is characterized by 13 ether rings. To attain a practical construction of this molecule, efficient supplies of the structural fragments are crucial. Herein we report the convergent synthesis of the HIJKLM ring fragment and present a new carbonyl olefination protocol to cyclize the J ring using low-valent titanium.

Original language	English
Pages (from-to)	6493-6512
Number of pages	20
Journal	Tetrahedron
Volume	58
Issue number	32
DOIs	https://doi.org/10.1016/S0040-4020(02)00660-9
Publication status	Published - Aug 5 2002
Externally published	Yes

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/S0040-4020(02)00660-9

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title = "Convergent synthesis of the HIJKLM ring fragment of ciguatoxin CTX3C",

abstract = "Ciguatoxin CTX3C is a representative congener of the ciguatoxins, which are known to be the principal causative agents of ciguatera food poisoning. The structure of CTX3C spans more than 3nm and is characterized by 13 ether rings. To attain a practical construction of this molecule, efficient supplies of the structural fragments are crucial. Herein we report the convergent synthesis of the HIJKLM ring fragment and present a new carbonyl olefination protocol to cyclize the J ring using low-valent titanium.",

author = "Hisatoshi Uehara and Tohru Oishi and Masayuki Inoue and Mitsuru Shoji and Yoko Nagumo and Masashi Kosaka and {Le Brazidec}, {Jean Yves} and Masahiro Hirama",

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T1 - Convergent synthesis of the HIJKLM ring fragment of ciguatoxin CTX3C

AU - Uehara, Hisatoshi

AU - Oishi, Tohru

AU - Inoue, Masayuki

AU - Shoji, Mitsuru

AU - Nagumo, Yoko

AU - Kosaka, Masashi

AU - Le Brazidec, Jean Yves

AU - Hirama, Masahiro

PY - 2002/8/5

Y1 - 2002/8/5

N2 - Ciguatoxin CTX3C is a representative congener of the ciguatoxins, which are known to be the principal causative agents of ciguatera food poisoning. The structure of CTX3C spans more than 3nm and is characterized by 13 ether rings. To attain a practical construction of this molecule, efficient supplies of the structural fragments are crucial. Herein we report the convergent synthesis of the HIJKLM ring fragment and present a new carbonyl olefination protocol to cyclize the J ring using low-valent titanium.

AB - Ciguatoxin CTX3C is a representative congener of the ciguatoxins, which are known to be the principal causative agents of ciguatera food poisoning. The structure of CTX3C spans more than 3nm and is characterized by 13 ether rings. To attain a practical construction of this molecule, efficient supplies of the structural fragments are crucial. Herein we report the convergent synthesis of the HIJKLM ring fragment and present a new carbonyl olefination protocol to cyclize the J ring using low-valent titanium.

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U2 - 10.1016/S0040-4020(02)00660-9

DO - 10.1016/S0040-4020(02)00660-9

M3 - Article

AN - SCOPUS:0037026010

SN - 0040-4020

VL - 58

SP - 6493

EP - 6512

JO - Tetrahedron

JF - Tetrahedron

IS - 32

ER -

Convergent synthesis of the HIJKLM ring fragment of ciguatoxin CTX3C

Abstract

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