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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...

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Detalles Bibliográficos
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
Descripción
Sumario:[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.