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 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.
Highlights
Functionalized C10-monoterpenoid alcohol with C10-monoterpenoid citral to form a C15-sesquiterpene
While a comprehensive account of their biogenesis is beyond the scope of this document, it is important to note thatcyclic terpenoids all arise from their linear precursors.[4]. Nature assembles these linear precursors by enzyme-mediated sequential addition of C5 units of isopentenyl pyrophosphate (IPP) to (C5)n-terpenyl pyrophosphates in the mevalonate pathway (Figure 1a).[5]
We recently reported an olefin cross metathesis reaction between relay-actuated Δ6,7-functionalized monoterpenoid alcohols with trisubstituted alkenes as partner olefins to form new trisubstituted alkenes (Figure 1b).[7]
Summary
Functionalized C10-monoterpenoid alcohol with C10-monoterpenoid citral to form a C15-sesquiterpene. Letter of terpenoids in line with the above aims (Figure 1c).[8] we report the application of this method for the synthesis of a diterpene-benzoate macrolide of biogenetic relevance to the bromophycolide natural product family.
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