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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.


ABSTRACT: 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 ?6,7-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.

SUBMITTER: Bahou KA 

PROVIDER: S-EPMC7171603 | biostudies-literature | 2020 Apr

REPOSITORIES: biostudies-literature

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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.

Bahou Karim A KA   Braddock D Christopher DC   Meyer Adam G AG   Savage G Paul GP  

Organic letters 20200331 8


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<sup>6,7</sup>-functionalized C<sub>10</sub>-monoterpenoid alcohol with C<sub>10</sub>-monoterpenoid citral to form a C<sub>15</sub>-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  ...[more]

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