Convergent synthesis of the ABCDE ring system of ciguatoxin CTX3C

Megumi Maruyama, Masayuki Inoue, Tohru Oishi, Hiroki Oguri, Yoshihiro Ogasawara, Yumi Shindo, Masahiro Hirama

Research output: Contribution to journalArticle

59 Citations (Scopus)

Abstract

Ciguatoxin CTX3C is a representative congener of the ciguatoxins, which are known to be the principal causative-agents of ciguatera seafood poisoning. The structure of CTX3C spans over three nanometers and is characterized by thirteen 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 ABCDE ring fragment featuring (i) alkylative coupling of the AB ring and E ring, and (ii) ring-closing olefin metathesis.

Original languageEnglish
Pages (from-to)1835-1851
Number of pages17
JournalTetrahedron
Volume58
Issue number10
DOIs
Publication statusPublished - Mar 4 2002
Externally publishedYes

Fingerprint

Ciguatoxins
Ciguatera Poisoning
Seafood
Alkenes
Ether
Molecules
ciguatoxin 3C

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

Maruyama, M., Inoue, M., Oishi, T., Oguri, H., Ogasawara, Y., Shindo, Y., & Hirama, M. (2002). Convergent synthesis of the ABCDE ring system of ciguatoxin CTX3C. Tetrahedron, 58(10), 1835-1851. https://doi.org/10.1016/S0040-4020(02)00041-8

Convergent synthesis of the ABCDE ring system of ciguatoxin CTX3C. / Maruyama, Megumi; Inoue, Masayuki; Oishi, Tohru; Oguri, Hiroki; Ogasawara, Yoshihiro; Shindo, Yumi; Hirama, Masahiro.

In: Tetrahedron, Vol. 58, No. 10, 04.03.2002, p. 1835-1851.

Research output: Contribution to journalArticle

Maruyama, M, Inoue, M, Oishi, T, Oguri, H, Ogasawara, Y, Shindo, Y & Hirama, M 2002, 'Convergent synthesis of the ABCDE ring system of ciguatoxin CTX3C', Tetrahedron, vol. 58, no. 10, pp. 1835-1851. https://doi.org/10.1016/S0040-4020(02)00041-8
Maruyama M, Inoue M, Oishi T, Oguri H, Ogasawara Y, Shindo Y et al. Convergent synthesis of the ABCDE ring system of ciguatoxin CTX3C. Tetrahedron. 2002 Mar 4;58(10):1835-1851. https://doi.org/10.1016/S0040-4020(02)00041-8
Maruyama, Megumi ; Inoue, Masayuki ; Oishi, Tohru ; Oguri, Hiroki ; Ogasawara, Yoshihiro ; Shindo, Yumi ; Hirama, Masahiro. / Convergent synthesis of the ABCDE ring system of ciguatoxin CTX3C. In: Tetrahedron. 2002 ; Vol. 58, No. 10. pp. 1835-1851.
@article{746f2e4a4d7744d6af7ab0556de0a156,
title = "Convergent synthesis of the ABCDE ring system of ciguatoxin CTX3C",
abstract = "Ciguatoxin CTX3C is a representative congener of the ciguatoxins, which are known to be the principal causative-agents of ciguatera seafood poisoning. The structure of CTX3C spans over three nanometers and is characterized by thirteen 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 ABCDE ring fragment featuring (i) alkylative coupling of the AB ring and E ring, and (ii) ring-closing olefin metathesis.",
author = "Megumi Maruyama and Masayuki Inoue and Tohru Oishi and Hiroki Oguri and Yoshihiro Ogasawara and Yumi Shindo and Masahiro Hirama",
year = "2002",
month = "3",
day = "4",
doi = "10.1016/S0040-4020(02)00041-8",
language = "English",
volume = "58",
pages = "1835--1851",
journal = "Tetrahedron",
issn = "0040-4020",
publisher = "Elsevier Limited",
number = "10",

}

TY - JOUR

T1 - Convergent synthesis of the ABCDE ring system of ciguatoxin CTX3C

AU - Maruyama, Megumi

AU - Inoue, Masayuki

AU - Oishi, Tohru

AU - Oguri, Hiroki

AU - Ogasawara, Yoshihiro

AU - Shindo, Yumi

AU - Hirama, Masahiro

PY - 2002/3/4

Y1 - 2002/3/4

N2 - Ciguatoxin CTX3C is a representative congener of the ciguatoxins, which are known to be the principal causative-agents of ciguatera seafood poisoning. The structure of CTX3C spans over three nanometers and is characterized by thirteen 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 ABCDE ring fragment featuring (i) alkylative coupling of the AB ring and E ring, and (ii) ring-closing olefin metathesis.

AB - Ciguatoxin CTX3C is a representative congener of the ciguatoxins, which are known to be the principal causative-agents of ciguatera seafood poisoning. The structure of CTX3C spans over three nanometers and is characterized by thirteen 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 ABCDE ring fragment featuring (i) alkylative coupling of the AB ring and E ring, and (ii) ring-closing olefin metathesis.

UR - http://www.scopus.com/inward/record.url?scp=0037017773&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0037017773&partnerID=8YFLogxK

U2 - 10.1016/S0040-4020(02)00041-8

DO - 10.1016/S0040-4020(02)00041-8

M3 - Article

VL - 58

SP - 1835

EP - 1851

JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

IS - 10

ER -