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: | Clark, Professor Stephen and Popadynec, Michael |
| 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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