A convergent synthesis of the right-hand fragment of ciguatoxin CTX3C

Hiroyoshi Takamura; Takashi Abe; Naoki Nishiuma; Rie Fujiwara; Takahiko Tsukeshiba; Isao Kadota

doi:10.1016/j.tet.2012.01.071

A convergent synthesis of the right-hand fragment of ciguatoxin CTX3C

Hiroyoshi Takamura, Takashi Abe, Naoki Nishiuma, Rie Fujiwara, Takahiko Tsukeshiba, Isao Kadota

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

13 Citations (Scopus)

Abstract

A convergent synthesis of the right-hand fragment of ciguatoxin CTX3C was investigated. The first and second generation stereocontrolled syntheses of the LM ring fragment were achieved via spiroacetalization as a key step, respectively. The polyether framework of the HIJKLM ring fragment was constructed in a convergent manner by using intramolecular allylation, ring-closing metathesis, and stereoselective hydrogenation to form the 36-methyl substituent as the key transformations.

Original language	English
Pages (from-to)	2245-2260
Number of pages	16
Journal	Tetrahedron
Volume	68
Issue number	10
DOIs	https://doi.org/10.1016/j.tet.2012.01.071
Publication status	Published - Mar 11 2012

Keywords

Ciguatoxin CTX3C
Convergent synthesis
Intramolecular allylation
Polyether marine natural product

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tet.2012.01.071

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title = "A convergent synthesis of the right-hand fragment of ciguatoxin CTX3C",

abstract = "A convergent synthesis of the right-hand fragment of ciguatoxin CTX3C was investigated. The first and second generation stereocontrolled syntheses of the LM ring fragment were achieved via spiroacetalization as a key step, respectively. The polyether framework of the HIJKLM ring fragment was constructed in a convergent manner by using intramolecular allylation, ring-closing metathesis, and stereoselective hydrogenation to form the 36-methyl substituent as the key transformations.",

keywords = "Ciguatoxin CTX3C, Convergent synthesis, Intramolecular allylation, Polyether marine natural product",

author = "Hiroyoshi Takamura and Takashi Abe and Naoki Nishiuma and Rie Fujiwara and Takahiko Tsukeshiba and Isao Kadota",

note = "Funding Information: This research was supported by Grant-in-Aid for Scientific Research from Japan Society for the Promotion of Science (JSPS). We appreciate Kato Memorial Bioscience Foundation , Mitsubishi Chemical Corporation Fund , and the Asahi Glass Foundation for their financial supports. A research fellowship for T.A. from JSPS is thankfully acknowledged.",

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doi = "10.1016/j.tet.2012.01.071",

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journal = "Tetrahedron",

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T1 - A convergent synthesis of the right-hand fragment of ciguatoxin CTX3C

AU - Takamura, Hiroyoshi

AU - Abe, Takashi

AU - Nishiuma, Naoki

AU - Fujiwara, Rie

AU - Tsukeshiba, Takahiko

AU - Kadota, Isao

N1 - Funding Information: This research was supported by Grant-in-Aid for Scientific Research from Japan Society for the Promotion of Science (JSPS). We appreciate Kato Memorial Bioscience Foundation , Mitsubishi Chemical Corporation Fund , and the Asahi Glass Foundation for their financial supports. A research fellowship for T.A. from JSPS is thankfully acknowledged.

PY - 2012/3/11

Y1 - 2012/3/11

N2 - A convergent synthesis of the right-hand fragment of ciguatoxin CTX3C was investigated. The first and second generation stereocontrolled syntheses of the LM ring fragment were achieved via spiroacetalization as a key step, respectively. The polyether framework of the HIJKLM ring fragment was constructed in a convergent manner by using intramolecular allylation, ring-closing metathesis, and stereoselective hydrogenation to form the 36-methyl substituent as the key transformations.

AB - A convergent synthesis of the right-hand fragment of ciguatoxin CTX3C was investigated. The first and second generation stereocontrolled syntheses of the LM ring fragment were achieved via spiroacetalization as a key step, respectively. The polyether framework of the HIJKLM ring fragment was constructed in a convergent manner by using intramolecular allylation, ring-closing metathesis, and stereoselective hydrogenation to form the 36-methyl substituent as the key transformations.

KW - Ciguatoxin CTX3C

KW - Convergent synthesis

KW - Intramolecular allylation

KW - Polyether marine natural product

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A convergent synthesis of the right-hand fragment of ciguatoxin CTX3C

Abstract

Keywords

ASJC Scopus subject areas

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