Stereoselective synthesis of the I–L fragment of the Pacific ciguatoxins

J. Clark, S. and Popadynec, M. (2020) Stereoselective synthesis of the I–L fragment of the Pacific ciguatoxins. Toxins, 12(12), 740. (doi: 10.3390/toxins12120740) (PMID:33255410) (PMCID:PMC7760828)

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Abstract

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.

Item Type:Articles
Status:Published
Refereed:Yes
Glasgow Author(s) Enlighten ID:Popadynec, Michael and Clark, Professor Stephen
Authors: J. Clark, S., and Popadynec, M.
College/School:College of Science and Engineering > School of Chemistry
Journal Name:Toxins
Publisher:MDPI
ISSN:2072-6651
ISSN (Online):2072-6651
Copyright Holders:Copyright © 2020 by the authors
First Published:First published in Toxins 12(12):740
Publisher Policy:Reproduced under a Creative Commons license

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Project CodeAward NoProject NamePrincipal InvestigatorFunder's NameFunder RefLead Dept
190490Engineering and Physical Sciences Doctoral Training Grant 2012-16Mary Beth KneafseyEngineering and Physical Sciences Research Council (EPSRC)EP/K503058/1Research and Innovation Services
190627Doctoral Training Grant 2013 - 2017Mary Beth KneafseyEngineering and Physical Sciences Research Council (EPSRC)EP/L50497X/1Research and Innovation Services