ArticleAngewandte Chemie (International ed. in English)2021
Enantioselective Total Synthesis of (+)-Garsubellin A.
Article in Angewandte Chemie (International ed. in English), 2021. 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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5 citing papers in PubMed, 16 citations in OpenAlex.
- Synthesis of 6-Organic letters · 2026Article
- Total Synthesis of (-)-Elodeoidins A and B.JACS Au · 2025Article
- Catalytic prenyl conjugate additions for synthesis of enantiomerically enriched PPAPs.Science (New York, N.Y.) · 2024Article
- Site-specific template generative approach for retrosynthetic planning.Nature communications · 2024Article
- Enantioselective Total Synthesis of (+)-Garsubellin A.Angewandte Chemie (International ed. in English) · 2021Article
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4 authors at 2 institutions in 3 countries.
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Abstract
Garsubellin A is a meroterpene capable of enhancing the enzyme choline acetyltransferase whose decreased level is believed to play a central role in the symptoms of Alzheimer's disease. Due to the potentially useful biological activity together with the novel bridged and fused cyclic molecular architecture, garsubellin A has garnered substantial synthetic interest, but its absolute stereostructure has been undetermined. We report here the first enantioselective total synthesis of (+)-garsubellin A. Our synthesis relies on stereoselective fashioning of a cyclohexanone framework and double conjugate addition of 1,2-ethanedithiol that promotes aldol cyclization to build the bicyclic [3.3.1] skeleton. The twelve-step, protecting group-free synthetic route has enabled the syntheses of both the natural (-)-garsubellin A and its unnatural (+)-antipode for biological evaluations.
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