A cross-metathesis approach to the stereocontrolled synthesis of the AB ring segment of ciguatoxin

Isao Kadota; Takashi Abe; Miyuki Uni; Hiroyoshi Takamura; Yoshinori Yamamoto

doi:10.1016/j.tetlet.2008.03.145

A cross-metathesis approach to the stereocontrolled synthesis of the AB ring segment of ciguatoxin

Isao Kadota, Takashi Abe, Miyuki Uni, Hiroyoshi Takamura, Yoshinori Yamamoto

School of Science

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

11 Citations (Scopus)

Abstract

Synthesis of the AB ring segments of ciguatoxin is described. The present synthesis includes a Lewis acid mediated cyclization of allylstannane with aldehyde, cross-metathesis reaction introducing the side chain, and Grieco-Nishizawa dehydration on the A ring.

Original language	English
Pages (from-to)	3643-3647
Number of pages	5
Journal	Tetrahedron Letters
Volume	49
Issue number	22
DOIs	https://doi.org/10.1016/j.tetlet.2008.03.145
Publication status	Published - May 26 2008

Keywords

Allylstannane-aldehyde condensation
Ciguatoxin
Cross-metathesis
Polycyclic ethers

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2008.03.145

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title = "A cross-metathesis approach to the stereocontrolled synthesis of the AB ring segment of ciguatoxin",

abstract = "Synthesis of the AB ring segments of ciguatoxin is described. The present synthesis includes a Lewis acid mediated cyclization of allylstannane with aldehyde, cross-metathesis reaction introducing the side chain, and Grieco-Nishizawa dehydration on the A ring.",

keywords = "Allylstannane-aldehyde condensation, Ciguatoxin, Cross-metathesis, Polycyclic ethers",

author = "Isao Kadota and Takashi Abe and Miyuki Uni and Hiroyoshi Takamura and Yoshinori Yamamoto",

note = "Funding Information: This work was financially supported by the Nagase Science and Technology Foundation, and the Grant-in-Aid for Scientific Research from the Ministry of Education, Culture, Sports, Science and Technology, Japan. ",

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doi = "10.1016/j.tetlet.2008.03.145",

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journal = "Tetrahedron Letters",

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TY - JOUR

T1 - A cross-metathesis approach to the stereocontrolled synthesis of the AB ring segment of ciguatoxin

AU - Kadota, Isao

AU - Abe, Takashi

AU - Uni, Miyuki

AU - Takamura, Hiroyoshi

AU - Yamamoto, Yoshinori

N1 - Funding Information: This work was financially supported by the Nagase Science and Technology Foundation, and the Grant-in-Aid for Scientific Research from the Ministry of Education, Culture, Sports, Science and Technology, Japan.

PY - 2008/5/26

Y1 - 2008/5/26

N2 - Synthesis of the AB ring segments of ciguatoxin is described. The present synthesis includes a Lewis acid mediated cyclization of allylstannane with aldehyde, cross-metathesis reaction introducing the side chain, and Grieco-Nishizawa dehydration on the A ring.

AB - Synthesis of the AB ring segments of ciguatoxin is described. The present synthesis includes a Lewis acid mediated cyclization of allylstannane with aldehyde, cross-metathesis reaction introducing the side chain, and Grieco-Nishizawa dehydration on the A ring.

KW - Allylstannane-aldehyde condensation

KW - Ciguatoxin

KW - Cross-metathesis

KW - Polycyclic ethers

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M3 - Article

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SN - 0040-4039

VL - 49

SP - 3643

EP - 3647

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 22

ER -

A cross-metathesis approach to the stereocontrolled synthesis of the AB ring segment of ciguatoxin

Abstract

Keywords

ASJC Scopus subject areas

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