Bidirectional Synthesis of the IJK Fragment of Ciguatoxin CTX3C by Sequential Double Ring-Closing Metathesis and Tsuji–Trost Allylation

[Image: see text] 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 o...

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Autores principales: Popadynec, Michael, Gibbard, Helen, Clark, J. Stephen
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2020
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7304930/
https://www.ncbi.nlm.nih.gov/pubmed/32306737
http://dx.doi.org/10.1021/acs.orglett.0c01238
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author Popadynec, Michael
Gibbard, Helen
Clark, J. Stephen
author_facet Popadynec, Michael
Gibbard, Helen
Clark, J. Stephen
author_sort Popadynec, Michael
collection PubMed
description [Image: see text] 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.
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spelling pubmed-73049302020-06-22 Bidirectional Synthesis of the IJK Fragment of Ciguatoxin CTX3C by Sequential Double Ring-Closing Metathesis and Tsuji–Trost Allylation Popadynec, Michael Gibbard, Helen Clark, J. Stephen Org Lett [Image: see text] 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. American Chemical Society 2020-04-19 2020-05-01 /pmc/articles/PMC7304930/ /pubmed/32306737 http://dx.doi.org/10.1021/acs.orglett.0c01238 Text en Copyright © 2020 American Chemical Society This is an open access article published under a Creative Commons Attribution (CC-BY) License (http://pubs.acs.org/page/policy/authorchoice_ccby_termsofuse.html) , which permits unrestricted use, distribution and reproduction in any medium, provided the author and source are cited.
spellingShingle Popadynec, Michael
Gibbard, Helen
Clark, J. Stephen
Bidirectional Synthesis of the IJK Fragment of Ciguatoxin CTX3C by Sequential Double Ring-Closing Metathesis and Tsuji–Trost Allylation
title Bidirectional Synthesis of the IJK Fragment of Ciguatoxin CTX3C by Sequential Double Ring-Closing Metathesis and Tsuji–Trost Allylation
title_full Bidirectional Synthesis of the IJK Fragment of Ciguatoxin CTX3C by Sequential Double Ring-Closing Metathesis and Tsuji–Trost Allylation
title_fullStr Bidirectional Synthesis of the IJK Fragment of Ciguatoxin CTX3C by Sequential Double Ring-Closing Metathesis and Tsuji–Trost Allylation
title_full_unstemmed Bidirectional Synthesis of the IJK Fragment of Ciguatoxin CTX3C by Sequential Double Ring-Closing Metathesis and Tsuji–Trost Allylation
title_short Bidirectional Synthesis of the IJK Fragment of Ciguatoxin CTX3C by Sequential Double Ring-Closing Metathesis and Tsuji–Trost Allylation
title_sort bidirectional synthesis of the ijk fragment of ciguatoxin ctx3c by sequential double ring-closing metathesis and tsuji–trost allylation
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7304930/
https://www.ncbi.nlm.nih.gov/pubmed/32306737
http://dx.doi.org/10.1021/acs.orglett.0c01238
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