Establishing the True Structure of the Sorbicillinoid-Derived Isolate Rezishanone C by Total Synthesis

Qiao Yan, Martin G. Banwell*, Michelle L. Coote, Richmond Lee, Anthony C. Willis

*Corresponding author for this work

    Research output: Contribution to journalArticlepeer-review

    9 Citations (Scopus)

    Abstract

    The enantiomer, ent-4, of the true structure, 4, of the sorbicillinoid rezishanone C (sorbivinetone) has been synthesized from a homochiral cis-1,2-dihydrocatechol that is itself generated through the whole-cell biotransformation of toluene. These studies together with dispersion-corrected DFT calculations support the proposal that rezishanone C is an artefact of the isolation process and arises through a Diels–Alder reaction between ethyl vinyl ether and sorbicillinol (3).

    Original languageEnglish
    Pages (from-to)1480-1484
    Number of pages5
    JournalChemistry - An Asian Journal
    Volume12
    Issue number13
    DOIs
    Publication statusPublished - 4 Jul 2017

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