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Relay Cross Metathesis for the Iterative Construction of Terpenoids and Synthesis of a Diterpene-Benzoate Macrolide of Biogenetic Relevance to the Bromophycolides
[Image: see text] We report a relay cross metathesis (ReXM) reaction for the construction of terpenoids in an iterative protocol. The protocol features the cross metathesis of a relay-actuated Δ(6,7)-functionalized C(10)-monoterpenoid alcohol with C(10)-monoterpenoid citral to form a C(15)-sesquiter...
Autores principales: | , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
American
Chemical Society
2020
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Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7171603/ https://www.ncbi.nlm.nih.gov/pubmed/32227974 http://dx.doi.org/10.1021/acs.orglett.0c00935 |
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author | Bahou, Karim A. Braddock, D. Christopher Meyer, Adam G. Savage, G. Paul |
author_facet | Bahou, Karim A. Braddock, D. Christopher Meyer, Adam G. Savage, G. Paul |
author_sort | Bahou, Karim A. |
collection | PubMed |
description | [Image: see text] We report a relay cross metathesis (ReXM) reaction for the construction of terpenoids in an iterative protocol. The protocol features the cross metathesis of a relay-actuated Δ(6,7)-functionalized C(10)-monoterpenoid alcohol with C(10)-monoterpenoid citral to form a C(15)-sesquiterpene. Subsequent functional group manipulation allows for the method to be repeated in an iterative fashion. The method is used for the synthesis of a diterpene-benzoate macrolide of biogenetic relevance to the bromophycolide family of natural products. |
format | Online Article Text |
id | pubmed-7171603 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2020 |
publisher | American
Chemical Society |
record_format | MEDLINE/PubMed |
spelling | pubmed-71716032020-04-21 Relay Cross Metathesis for the Iterative Construction of Terpenoids and Synthesis of a Diterpene-Benzoate Macrolide of Biogenetic Relevance to the Bromophycolides Bahou, Karim A. Braddock, D. Christopher Meyer, Adam G. Savage, G. Paul Org Lett [Image: see text] We report a relay cross metathesis (ReXM) reaction for the construction of terpenoids in an iterative protocol. The protocol features the cross metathesis of a relay-actuated Δ(6,7)-functionalized C(10)-monoterpenoid alcohol with C(10)-monoterpenoid citral to form a C(15)-sesquiterpene. Subsequent functional group manipulation allows for the method to be repeated in an iterative fashion. The method is used for the synthesis of a diterpene-benzoate macrolide of biogenetic relevance to the bromophycolide family of natural products. American Chemical Society 2020-03-31 2020-04-17 /pmc/articles/PMC7171603/ /pubmed/32227974 http://dx.doi.org/10.1021/acs.orglett.0c00935 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 | Bahou, Karim A. Braddock, D. Christopher Meyer, Adam G. Savage, G. Paul Relay Cross Metathesis for the Iterative Construction of Terpenoids and Synthesis of a Diterpene-Benzoate Macrolide of Biogenetic Relevance to the Bromophycolides |
title | Relay Cross Metathesis for the Iterative Construction
of Terpenoids and Synthesis of a Diterpene-Benzoate Macrolide of Biogenetic
Relevance to the Bromophycolides |
title_full | Relay Cross Metathesis for the Iterative Construction
of Terpenoids and Synthesis of a Diterpene-Benzoate Macrolide of Biogenetic
Relevance to the Bromophycolides |
title_fullStr | Relay Cross Metathesis for the Iterative Construction
of Terpenoids and Synthesis of a Diterpene-Benzoate Macrolide of Biogenetic
Relevance to the Bromophycolides |
title_full_unstemmed | Relay Cross Metathesis for the Iterative Construction
of Terpenoids and Synthesis of a Diterpene-Benzoate Macrolide of Biogenetic
Relevance to the Bromophycolides |
title_short | Relay Cross Metathesis for the Iterative Construction
of Terpenoids and Synthesis of a Diterpene-Benzoate Macrolide of Biogenetic
Relevance to the Bromophycolides |
title_sort | relay cross metathesis for the iterative construction
of terpenoids and synthesis of a diterpene-benzoate macrolide of biogenetic
relevance to the bromophycolides |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7171603/ https://www.ncbi.nlm.nih.gov/pubmed/32227974 http://dx.doi.org/10.1021/acs.orglett.0c00935 |
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