Boston University Libraries OpenBU
    JavaScript is disabled for your browser. Some features of this site may not work without it.
    View Item 
    •   OpenBU
    • BU Open Access Articles
    • BU Open Access Articles
    • View Item
    •   OpenBU
    • BU Open Access Articles
    • BU Open Access Articles
    • View Item

    Biomimetic synthesis of meroterpenoids by dearomatization-driven polycyclization

    Thumbnail
    Date Issued
    2019-11-04
    Publisher Version
    10.1002/anie.201910710
    Author(s)
    Powers, Zachary
    Scharf, Adam
    Cheng, Andrea
    Yang, Feng
    Himmelbauer, Martin
    Mitsuhashi, Takaaki
    Barra, Lena
    Taniguchi, Yoshimasa
    Kikuchi, Takashi
    Fujita, Makoto
    Abe, Ikuro
    Porco, John A.
    Share to FacebookShare to TwitterShare by Email
    Export Citation
    Download to BibTex
    Download to EndNote/RefMan (RIS)
    Metadata
    Show full item record
    Permanent Link
    https://hdl.handle.net/2144/41804
    Version
    Accepted manuscript
    Citation (published version)
    Zachary Powers, Adam Scharf, Andrea Cheng, Feng Yang, Martin Himmelbauer, Takaaki Mitsuhashi, Lena Barra, Yoshimasa Taniguchi, Takashi Kikuchi, Makoto Fujita, Ikuro Abe, John A Porco. 2019. "Biomimetic Synthesis of Meroterpenoids by Dearomatization-Driven Polycyclization.." Angew Chem Int Ed Engl, Volume 58, Issue 45, pp. 16141 - 16146. https://doi.org/10.1002/anie.201910710
    Abstract
    A biomimetic route to farnesyl pyrophosphate and dimethyl orsellinic acid (DMOA)-derived meroterpenoid scaffolds has yet to be reported despite great interest from the chemistry and biomedical research communities. A concise synthetic route with the potential to access DMOA-derived meroterpenoids is highly desirable to create a library of related compounds. Herein, we report novel dearomatization methodology followed by polyene cyclization to access DMOA-derived meroterpenoid frameworks in six steps from commercially available starting materials. Furthermore, several farnesyl alkene substrates were used to generate structurally novel, DMOA-derived meroterpenoid derivatives. DFT calculations combined with experimentation provided a rationale for the observed thermodynamic distribution of polycyclization products.
    Description
    Published in final edited form as: Angew Chem Int Ed Engl. 2019 November 04; 58(45): 16141–16146. doi:10.1002/anie.201910710.
    Collections
    • CAS: Chemistry: Scholarly Papers [120]
    • BU Open Access Articles [3670]


    Boston University
    Contact Us | Send Feedback | Help
     

     

    Browse

    All of OpenBUCommunities & CollectionsIssue DateAuthorsTitlesSubjectsThis CollectionIssue DateAuthorsTitlesSubjects

    Deposit Materials

    LoginNon-BU Registration

    Statistics

    Most Popular ItemsStatistics by CountryMost Popular Authors

    Boston University
    Contact Us | Send Feedback | Help