ArticleAngewandte Chemie (International ed. in English)2021
Enantioselective Total Synthesis and Structural Revision of Dysiherbol 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, 37 citations in OpenAlex.
- Total Synthesis of Dactyloquinone A and Spiroetherone A via a Metal-Hydride Hydrogen Atom Transfer (MHAT) Process and a Quinol-Enedione Rearrangement.Angewandte Chemie (International ed. in English) · 2025Article
- Divergent total synthesis of the revised structures of marine anti-cancer meroterpenoids (+)-dysiherbols A-E.Chemical science · 2023Article
- Lewis Acid-Catalyzed Halonium Generation for Morpholine Synthesis and Claisen Rearrangement.The Journal of organic chemistry · 2022Article
- Recent Achievements in Total Synthesis for Integral Structural Revisions of Marine Natural Products.Marine drugs · 2022Review
- Enantioselective Total Synthesis and Structural Revision of Dysiherbol A.Angewandte Chemie (International ed. in English) · 2021Article
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5 authors at 1 institution in 1 country.
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Abstract
A 12-step total synthesis of the natural product dysiherbol A, a strongly anti-inflammatory and anti-tumor avarane meroterpene isolated from the marine sponge Dysidea sp., was elaborated. As key steps, the synthesis features an enantioselective Cu-catalyzed 1,4-addition/enolate-trapping opening move, an Au-catalyzed double cyclization to build up the tetracyclic core-carbon skeleton, and a late installation of the C5-bridgehead methyl group via proton-induced cyclopropane opening associated with spontaneous cyclic ether formation. The obtained pentacyclic compound (corresponding to an anhydride of the originally suggested structure for dysiherbol A) showed identical spectroscopic data as the natural product, but an opposite molecular rotation. CD-spectroscopic measurements finally confirmed that both the constitution and the absolute configuration of the originally proposed structure of (+)-dysiherbol A need to be revised.
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