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

Karim A Bahou; D Christopher Braddock; Adam G Meyer; G Paul Savage

doi:10.1021/acs.orglett.0c00935

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

Org Lett. 2020 Apr 17;22(8):3176-3179. doi: 10.1021/acs.orglett.0c00935. Epub 2020 Mar 31.

Authors

Karim A Bahou¹, D Christopher Braddock¹, Adam G Meyer², G Paul Savage²

Affiliations

¹ Department of Chemistry, Molecular Sciences Research Hub, Imperial College London, London W12 0BZ, United Kingdom.
² CSIRO Manufacturing, Jerry Price Laboratory, Research Way, Clayton, Victoria 3168, Australia.

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 Δ^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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Benzoates / chemistry*
Diterpenes / chemical synthesis*
Diterpenes / chemistry
Macrolides / chemical synthesis*
Macrolides / chemistry
Molecular Structure
Terpenes / chemistry*

Substances

Benzoates
Diterpenes
Macrolides
Terpenes
bromophycolide A