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...

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Autores principales: Bahou, Karim A., Braddock, D. Christopher, Meyer, Adam G., Savage, G. Paul
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2020
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.
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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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