ArticleAngewandte Chemie (International ed. in English)2025
Total Synthesis of Dactyloquinone A and Spiroetherone A via a Metal-Hydride Hydrogen Atom Transfer (MHAT) Process and a Quinol-Enedione Rearrangement.
Article in Angewandte Chemie (International ed. in English), 2025. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 3 papers.
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3 citing papers in PubMed.
- Oxygen-Oxygen Bond-Forming Reactions for the Synthesis of Cyclic Peroxides.Journal of the American Chemical Society · 2026Article
- 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
- Quinol-Enedione Rearrangement.Organic letters · 2025Article
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5 authors.
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Abstract
We report the total synthesis of dactyloquinone A and spiroetherone A from a meroterpenoid scaffold obtained by the deconjugative alkylation of a Wieland-Miescher type ketone. For dactyloquinone A, we employed an intramolecular hydrofunctionalisation of the internal trisubstituted alkene with a quinone monoacetal via a metal-hydride hydrogen atom transfer (MHAT) process to form the key C─O bond. For spiroetherone A, we relied on a stereospecific quinol-spiroenedione rearrangement. The initially postulated structure of spiroetherone A was first synthesized, but was found to be different from the natural product. Finally, spiroetherone A was shown to be epimeric at the spirocyclic carbon. This finding was confirmed by total synthesis involving epimerization of the spirocycle via a late-stage singlet oxygen [4+2] cycloaddition to a cyclohexadiene derived from the initial enedione.
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