Bidirectional synthesis of the IJK fragment of ciguatoxin CTX3C by sequential double ring-closing metathesis and Tsuji-Trost allylation

Popadynec, M., Clark, J. S. and Gibbard, H. (2020) Bidirectional synthesis of the IJK fragment of ciguatoxin CTX3C by sequential double ring-closing metathesis and Tsuji-Trost allylation. Organic Letters, 22(9), pp. 3734-3738. (doi: 10.1021/acs.orglett.0c01238) (PMID:32306737) (PMCID:PMC7304930)

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Abstract

A novel four-step bidirectional strategy has been used to synthesize the IJK fragment of the marine polyether natural product CTX3C from a simple monocyclic precursor in a concise and efficient manner. The four-step bidirectional sequence involves ring-closing metathesis, alcohol oxidation, enol carbonate formation, and palladium-mediated Tsuji–Trost allylation.

Item Type:Articles
Status:Published
Refereed:Yes
Glasgow Author(s) Enlighten ID:Popadynec, Michael and Clark, Professor Stephen
Authors: Popadynec, M., Clark, J. S., and Gibbard, H.
College/School:College of Science and Engineering > School of Chemistry
Journal Name:Organic Letters
Publisher:American Chemical Society
ISSN:1523-7060
ISSN (Online):1523-7052
Published Online:19 April 2020
Copyright Holders:Copyright © 2020 American Chemical Society
First Published:First published in Organic Letters 22(9): 3734-3738
Publisher Policy:Reproduced under a Creative Commons license

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Project CodeAward NoProject NamePrincipal InvestigatorFunder's NameFunder RefLead Dept
1900502008-12 Doctoral Training GrantMary Beth KneafseyEngineering and Physical Sciences Research Council (EPSRC)EP/P50418X/1Research and Innovation Services
190121Engineering and Physical Sciences Doctoral Training Grant 2009-13Mary Beth KneafseyEngineering and Physical Sciences Research Council (EPSRC)EP/P504937/1Research and Innovation Services
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