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Open AccessArticle

Stereoselective Synthesis of the I–L Fragment of the Pacific Ciguatoxins

School of Chemistry, Joseph Black Building, University of Glasgow, Glasgow G12 8QQ, UK
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Author to whom correspondence should be addressed.
Toxins 2020, 12(12), 740; https://doi.org/10.3390/toxins12120740
Received: 30 October 2020 / Revised: 20 November 2020 / Accepted: 20 November 2020 / Published: 24 November 2020
(This article belongs to the Special Issue Ciguatoxins)
The I–L ring system found in all the Pacific ciguatoxins has been prepared from a tricyclic precursor in a highly stereoselective manner. Subtle differences in the reactivity of the enones present in the seven- and eight-membered rings of the tricyclic ether starting material have been exploited to allow selective protection of the enone in the eight-membered ring. Subsequent distereoselective allylation of the seven-membered ring has been accomplished by a palladium-mediated Tsuji-Trost reaction. The K-ring methyl and hydroxyl groups have been installed in a highly stereoselective manner by sequential conjugate reduction and enolate oxidation reactions. Ring L has been constructed by a use of a novel relay ring-closing metathesis reaction to complete the tetracyclic framework, which possesses the functionality necessary for elaboration of rings I and L and the introduction of ring M. View Full-Text
Keywords: pacific ciguatoxins; natural product; polycyclic ether; ring-closing metathesis; Tsuji-Trost allylation pacific ciguatoxins; natural product; polycyclic ether; ring-closing metathesis; Tsuji-Trost allylation
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MDPI and ACS Style

Clark, J.S.; Popadynec, M. Stereoselective Synthesis of the I–L Fragment of the Pacific Ciguatoxins. Toxins 2020, 12, 740.

AMA Style

Clark JS, Popadynec M. Stereoselective Synthesis of the I–L Fragment of the Pacific Ciguatoxins. Toxins. 2020; 12(12):740.

Chicago/Turabian Style

Clark, J. S.; Popadynec, Michael. 2020. "Stereoselective Synthesis of the I–L Fragment of the Pacific Ciguatoxins" Toxins 12, no. 12: 740.

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