Improved synthesis of the AE ring segment of ciguatoxin CTX3C by using intramolecular allylations

Tokihiro Tanaka, Hiroki Asakura, Rie Fujiwara, Kentaro Kumamoto, Hiroaki Izuka, Kengo Shiroma, Hiroyoshi Takamura, Isao Kadota

Research output: Contribution to journal › Article

1 Citation (Scopus)

Abstract

An improved synthesis of the AE ring segment of ciguatoxin CTX3C is described. The E ring segment was synthesized by the intramolecular reaction of allylic stannane and aldehyde with high stereoselectivity. Construction of the AE ring framework was performed by using the intramolecular allylation of α-acetoxy ether followed by ring-closing metathesis.

Original languageEnglish
Pages (from-to)507-514
Number of pages8
JournalBulletin of the Chemical Society of Japan
Volume91
Issue number4
DOIs
Publication statusPublished - Jan 1 2018

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Allylation
Stereoselectivity
Aldehydes
Ether
ciguatoxin 3C
stannane

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Improved synthesis of the AE ring segment of ciguatoxin CTX3C by using intramolecular allylations. / Tanaka, Tokihiro; Asakura, Hiroki; Fujiwara, Rie; Kumamoto, Kentaro; Izuka, Hiroaki; Shiroma, Kengo; Takamura, Hiroyoshi; Kadota, Isao.

In: Bulletin of the Chemical Society of Japan, Vol. 91, No. 4, 01.01.2018, p. 507-514.

Research output: Contribution to journal › Article

Tanaka, T, Asakura, H, Fujiwara, R, Kumamoto, K, Izuka, H, Shiroma, K, Takamura, H & Kadota, I 2018, 'Improved synthesis of the AE ring segment of ciguatoxin CTX3C by using intramolecular allylations', Bulletin of the Chemical Society of Japan, vol. 91, no. 4, pp. 507-514. https://doi.org/10.1246/bcsj.20170390
Tanaka T, Asakura H, Fujiwara R, Kumamoto K, Izuka H, Shiroma K et al. Improved synthesis of the AE ring segment of ciguatoxin CTX3C by using intramolecular allylations. Bulletin of the Chemical Society of Japan. 2018 Jan 1;91(4):507-514. https://doi.org/10.1246/bcsj.20170390
Tanaka, Tokihiro ; Asakura, Hiroki ; Fujiwara, Rie ; Kumamoto, Kentaro ; Izuka, Hiroaki ; Shiroma, Kengo ; Takamura, Hiroyoshi ; Kadota, Isao. / Improved synthesis of the AE ring segment of ciguatoxin CTX3C by using intramolecular allylations. In: Bulletin of the Chemical Society of Japan. 2018 ; Vol. 91, No. 4. pp. 507-514.
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