Relay Cross Metathesis for the Iterative Construction of Terpenoids and Synthesis of a Diterpene-Benzoate Macrolide of Biogenetic Relevance to the Bromophycolides

Relay Cross Metathesis for the Iterative Construction of Terpenoids and Synthesis of a Diterpene-Benzoate Macrolide of Biogenetic Relevance to the Bromophycolides

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 Δ6,7-functionalized C10-monoterpenoid alcohol with C10-monoterpenoid citral to form a C15-sesquiterpene. Subsequent functiona...

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Veröffentlicht in:Organic letters 2020-04, Vol.22 (8), p.3176-3179
Hauptverfasser: Bahou, Karim A, Braddock, D. Christopher, Meyer, Adam G, Savage, G. Paul
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alcohols
chemical reactions
citral
Letter
macrolides
moieties
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container_title Organic letters
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creator Bahou, Karim A
Braddock, D. Christopher
Meyer, Adam G
Savage, G. Paul
description 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 Δ6,7-functionalized C10-monoterpenoid alcohol with C10-monoterpenoid citral to form a C15-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.
doi_str_mv 10.1021/acs.orglett.0c00935
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subjects alcohols
chemical reactions
citral
Letter
macrolides
moieties
title Relay Cross Metathesis for the Iterative Construction of Terpenoids and Synthesis of a Diterpene-Benzoate Macrolide of Biogenetic Relevance to the Bromophycolides
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