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

Research output: Contribution to journalArticle

9 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 languageEnglish
Pages (from-to)3643-3647
Number of pages5
JournalTetrahedron Letters
Volume49
Issue number22
DOIs
Publication statusPublished - May 26 2008

Fingerprint

Ciguatoxins
Lewis Acids
Cross Reactions
Cyclization
Dehydration
Aldehydes

Keywords

  • Allylstannane-aldehyde condensation
  • Ciguatoxin
  • Cross-metathesis
  • Polycyclic ethers

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

A cross-metathesis approach to the stereocontrolled synthesis of the AB ring segment of ciguatoxin. / Kadota, Isao; Abe, Takashi; Uni, Miyuki; Takamura, Hiroyoshi; Yamamoto, Yoshinori.

In: Tetrahedron Letters, Vol. 49, No. 22, 26.05.2008, p. 3643-3647.

Research output: Contribution to journalArticle

Kadota, Isao ; Abe, Takashi ; Uni, Miyuki ; Takamura, Hiroyoshi ; Yamamoto, Yoshinori. / A cross-metathesis approach to the stereocontrolled synthesis of the AB ring segment of ciguatoxin. In: Tetrahedron Letters. 2008 ; Vol. 49, No. 22. pp. 3643-3647.
@article{fe43801881784e648c7e7e2395d63d51,
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",
year = "2008",
month = "5",
day = "26",
doi = "10.1016/j.tetlet.2008.03.145",
language = "English",
volume = "49",
pages = "3643--3647",
journal = "Tetrahedron Letters",
issn = "0040-4039",
publisher = "Elsevier Limited",
number = "22",

}

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

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

UR - http://www.scopus.com/inward/record.url?scp=42949104563&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=42949104563&partnerID=8YFLogxK

U2 - 10.1016/j.tetlet.2008.03.145

DO - 10.1016/j.tetlet.2008.03.145

M3 - Article

AN - SCOPUS:42949104563

VL - 49

SP - 3643

EP - 3647

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 22

ER -