Triantafyllakis, M., Alexander, S., Woolford, S., Wilson, C. and Clark, J. S. (2023) Synthesis of the A−F fragment of the Pacific ciguatoxin CTX3C by iterative ring-closing metathesis and Tsuji–Trost allylation. Chemistry: A European Journal, 27(72), e202303121. (doi: 10.1002/chem.202303121) (PMID:37830907)
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Abstract
The fully functionalized A−F fragment of the Pacific ciguatoxin CTX3C has been synthesized from a derivative of D-glucal, which serves as the B-ring. Rings A and C were introduced to either side of ring B by ring-closing diene and enyne metathesis (RCM). The seven-membered D-ring and eight-membered E-ring were assembled by iterative use of a six-step reaction sequence in which RCM was used for ring construction and Tsuji–Trost allylation was employed for subsequent stereoselective functionalization. The nine-membered F-ring was formed by use of an RCM reaction and bears the functionality required for attachment of the I−M fragment and subsequent closure of rings G and H.
| Item Type: | Articles |
|---|---|
| Additional Information: | We thank the Engineering and Physical Sciences Research Council (EPSRC), UK for funding (grant numbers EP/R035423/1, EP/K503058, EP/L50497X, EP/M506539, EP/R513222/1 and EP/T517896/1). |
| Status: | Published |
| Refereed: | Yes |
| Glasgow Author(s) Enlighten ID: | Woolford, Sophie and Triantafyllakis, Mr Myron and Clark, Professor Stephen and Wilson, Dr Claire and Alexander, Mr Samuel |
| Authors: | Triantafyllakis, M., Alexander, S., Woolford, S., Wilson, C., and Clark, J. S. |
| College/School: | College of Science and Engineering > School of Chemistry |
| Journal Name: | Chemistry: A European Journal |
| Publisher: | Wiley |
| ISSN: | 0947-6539 |
| ISSN (Online): | 1521-3765 |
| Published Online: | 13 October 2023 |
| Copyright Holders: | Copyright © 2023 The Authors |
| First Published: | First published in Chemistry: A European Journal 29:e202303121 |
| Publisher Policy: | Reproduced under a Creative Commons License |
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