ArticleAngewandte Chemie (International ed. in English)2019
Biomimetic Synthesis of Meroterpenoids by Dearomatization-Driven Polycyclization.
Article in Angewandte Chemie (International ed. in English), 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 14 papers.
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Who cites it
14 citing papers in PubMed.
- Total syntheses of (+)-dalesconols A and B enabled by triple-relayed remote chirality transfer.Nature communications · 2026Article
- OD (order-disorder) interpretation and diffuse scattering analysis of an organic polytype with allotwin character: a detailed how-to.Acta crystallographica Section B, Structural science, crystal engineering and materials · 2025Article
- Evolution of a Strategy for the Unified, Asymmetric Total Syntheses of DMOA-Derived Spiromeroterpenoids.The Journal of organic chemistry · 2024Review
- Recent Advances in Chemistry and Antioxidant/Anticancer Biology of Monoterpene and Meroterpenoid Natural Product.Molecules (Basel, Switzerland) · 2024Review
- Recent Developments and Applications of Biocatalytic and Chemoenzymatic Synthesis for the Generation of Diverse Classes of Drugs.Current pharmaceutical biotechnology · 2024Article
- Charting the Evolution of Chemoenzymatic Strategies in the Syntheses of Complex Natural Products.Journal of the American Chemical Society · 2023Review
- Discovery of branching meroterpenoid biosynthetic pathways inChemical science · 2022Article
- Hemiacetalmeroterpenoids A-C and Astellolide Q with Antimicrobial Activity from the Marine-Derived FungusMarine drugs · 2022Article
- Unified, Asymmetric Total Synthesis of the Asnovolins and Related Spiromeroterpenoids: A Fragment Coupling Approach.Journal of the American Chemical Society · 2022Article
- Recent Advances in Biocatalysis for Drug Synthesis.Biomedicines · 2022Review
- New Andrastin-Type Meroterpenoids from the Marine-Derived FungusMarine drugs · 2021Article
- A Novel Azaphilone Muyophilone A From the Endophytic FungusFrontiers in chemistry · 2021Article
- Exploiting the Potential of Meroterpenoid Cyclases to Expand the Chemical Space of Fungal Meroterpenoids.Angewandte Chemie (International ed. in English) · 2020Article
- Polycyclizations of Ketoesters: Synthesis of Complex Tricycles with up to Five Stereogenic Centers from Available Starting Materials.Organic letters · 2020Article
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Authors and funding
12 authors.
Funding
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.
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