Two convergent routes to the left-wing fragment of ciguatoxin CTX3C using O,S-acetals as key intermediates

Masayuki Inoue; Shuji Yamashita; Yuuki Ishihara; Masahiro Hirama

doi:10.1021/ol062350h

Two convergent routes to the left-wing fragment of ciguatoxin CTX3C using O,S-acetals as key intermediates

Masayuki Inoue, Shuji Yamashita, Yuuki Ishihara, Masahiro Hirama

SCI - Chemistry

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

35 Citations (Scopus)

Abstract

(Diagram presented) Ciguatoxins, principal causative toxins of ciguatera seafood poisoning, are large ladderlike polycyclic ethers. Here, we report two convergent routes to synthesis of the multiolefinic left half of ciguatoxins based on a newly developed acyl radical strategy. Remarkably, only 13 steps from the monocyclic E-ring were required to construct the left wing.

Original language	English
Pages (from-to)	5805-5808
Number of pages	4
Journal	Organic letters
Volume	8
Issue number	25
DOIs	https://doi.org/10.1021/ol062350h
Publication status	Published - 2006 Dec 7

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol062350h

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abstract = "(Diagram presented) Ciguatoxins, principal causative toxins of ciguatera seafood poisoning, are large ladderlike polycyclic ethers. Here, we report two convergent routes to synthesis of the multiolefinic left half of ciguatoxins based on a newly developed acyl radical strategy. Remarkably, only 13 steps from the monocyclic E-ring were required to construct the left wing.",

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AU - Inoue, Masayuki

AU - Yamashita, Shuji

AU - Ishihara, Yuuki

AU - Hirama, Masahiro

PY - 2006/12/7

Y1 - 2006/12/7

N2 - (Diagram presented) Ciguatoxins, principal causative toxins of ciguatera seafood poisoning, are large ladderlike polycyclic ethers. Here, we report two convergent routes to synthesis of the multiolefinic left half of ciguatoxins based on a newly developed acyl radical strategy. Remarkably, only 13 steps from the monocyclic E-ring were required to construct the left wing.

AB - (Diagram presented) Ciguatoxins, principal causative toxins of ciguatera seafood poisoning, are large ladderlike polycyclic ethers. Here, we report two convergent routes to synthesis of the multiolefinic left half of ciguatoxins based on a newly developed acyl radical strategy. Remarkably, only 13 steps from the monocyclic E-ring were required to construct the left wing.

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Two convergent routes to the left-wing fragment of ciguatoxin CTX3C using O,S-acetals as key intermediates

Abstract

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