Stereoselective 6-exo radical cyclization using cis-Vinyl sulfoxide: Practical total synthesis of CTX3C

Shuji Yamashita; Yuuki Ishihara; Hiroyuki Morita; Junichi Uchiyama; Katsutoshi Takeuchi; Masayuki Inoue; Masahiro Hirama

doi:10.1021/np100729d

Stereoselective 6-exo radical cyclization using cis-Vinyl sulfoxide: Practical total synthesis of CTX3C

Shuji Yamashita, Yuuki Ishihara, Hiroyuki Morita, Junichi Uchiyama, Katsutoshi Takeuchi, Masayuki Inoue, Masahiro Hirama

SCI - Chemistry

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

31 Citations (Scopus)

Abstract

Ciguatoxins, the principal causative toxins of ciguatera seafood poisoning, are large ladder-like polycyclic ethers. We report a highly stereoselective 6-exo radical cyclization/ring-closing olefin metathesis sequence to construct the syn/trans-fused polyether system. The new method was applied to the practical synthesis of ciguatoxin CTX3C.

Original language	English
Pages (from-to)	357-364
Number of pages	8
Journal	Journal of Natural Products
Volume	74
Issue number	3
DOIs	https://doi.org/10.1021/np100729d
Publication status	Published - 2011 Mar 25

ASJC Scopus subject areas

Analytical Chemistry
Molecular Medicine
Pharmacology
Pharmaceutical Science
Drug Discovery
Complementary and alternative medicine
Organic Chemistry

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Stereoselective 6-exo radical cyclization using cis-Vinyl sulfoxide : Practical total synthesis of CTX3C. / Yamashita, Shuji; Ishihara, Yuuki; Morita, Hiroyuki; Uchiyama, Junichi; Takeuchi, Katsutoshi; Inoue, Masayuki; Hirama, Masahiro.

In: Journal of Natural Products, Vol. 74, No. 3, 25.03.2011, p. 357-364.

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

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AU - Morita, Hiroyuki

AU - Uchiyama, Junichi

AU - Takeuchi, Katsutoshi

AU - Inoue, Masayuki

AU - Hirama, Masahiro

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AB - Ciguatoxins, the principal causative toxins of ciguatera seafood poisoning, are large ladder-like polycyclic ethers. We report a highly stereoselective 6-exo radical cyclization/ring-closing olefin metathesis sequence to construct the syn/trans-fused polyether system. The new method was applied to the practical synthesis of ciguatoxin CTX3C.

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Stereoselective 6-exo radical cyclization using cis-Vinyl sulfoxide: Practical total synthesis of CTX3C

Abstract

ASJC Scopus subject areas

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