ArticleNature communications2024
Enantioselective total synthesis of (‒)-lucidumone enabled by tandem prins cyclization/cycloetherification sequence.
Article in Nature communications, 2024. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 5 papers.
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Who cites it
5 citing papers in PubMed.
- Total synthesis of natural products facilitated by prins reaction: a review.RSC advances · 2026Review
- Total Synthesis of Annotinolide B via Sequential Quinoline Dearomatization.Journal of the American Chemical Society · 2025Article
- Charge Relocation Enables a Modular and Diastereoselective Synthesis of cis-Substituted Tetrahydrofurans.Angewandte Chemie (International ed. in English) · 2025Article
- Photoinduced formal [4 + 2] cycloaddition of two electron-deficient olefins and its application to the synthesis of lucidumone.Nature communications · 2024Article
- Asymmetric total syntheses of sarglamides A, C, D, E, and F.Chemical science · 2024Article
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Authors and funding
4 authors.
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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.
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