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Enantioselective total synthesis of (‒)-lucidumone enabled by tandem prins cyclization/cycloetherification sequence

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  • Xian-Zhang Liao

    (Chinese Academy of Medical Sciences & Peking Union Medical College
    Chinese Academy of Medical Sciences & Peking Union Medical College)

  • Ran Wang

    (Chinese Academy of Medical Sciences & Peking Union Medical College
    Chinese Academy of Medical Sciences & Peking Union Medical College)

  • Xin Wang

    (Chinese Academy of Medical Sciences & Peking Union Medical College
    Chinese Academy of Medical Sciences & Peking Union Medical College)

  • Guang Li

    (Chinese Academy of Medical Sciences & Peking Union Medical College
    Chinese Academy of Medical Sciences & Peking Union Medical College)

Abstract

The Ganoderma meroterpenoids are a growing class of natural products with architectural complexity, and exhibit a wide range of biological activities. Here, we report an enantioselective total synthesis of the Ganoderma meroterpenoid (‒)-lucidumone. The synthetic route features several key transformations, including a) a Cu-catalyzed enantioselective silicon-tethered intramolecular Diels-Alder cycloaddition to construct the highly functionalized bicyclo[2.2.2]octane moiety; b) Brønsted acid promoted tandem O-deprotection/Prins cyclization/Cycloetherification sequence followed by oxidation to install concurrently the tetrahydrofuran and the fused indanone framework; c) Fleming-Tamao oxidation to generate the secondary hydroxyl; d) an iron-catalyzed Wacker-type oxidation of hindered vinyl group to methyl ketone.

Suggested Citation

  • Xian-Zhang Liao & Ran Wang & Xin Wang & Guang Li, 2024. "Enantioselective total synthesis of (‒)-lucidumone enabled by tandem prins cyclization/cycloetherification sequence," Nature Communications, Nature, vol. 15(1), pages 1-7, December.
    • Handle: RePEc:nat:natcom:v:15:y:2024:i:1:d:10.1038_s41467-024-46896-3
    DOI: 10.1038/s41467-024-46896-3
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