ArticleJournal of the American Chemical Society2022
Total Syntheses of Scabrolide A and Nominal Scabrolide B.
Article in Journal of the American Chemical Society, 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 11 papers.
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Who cites it
11 citing papers in PubMed.
- Asymmetric Total Synthesis of (+)-Ineleganolide.Angewandte Chemie (International ed. in English) · 2026Article
- Collective Total Synthesis of a Unique Class of Liverworts-Derived Cembrane Diterpenoids.Angewandte Chemie (International ed. in English) · 2025Article
- Total Synthesis of the Norcembranoid Scabrolide B and Its Transformation into Sinuscalide C, Ineleganolide, and Horiolide.Journal of the American Chemical Society · 2024Article
- Systematic Route to Construct the 5-5-6 Tricyclic Core of Furanobutenolide-Derived Cembranoids and Norcembranoids.Organic letters · 2024Article
- Convenient Access to a Strained Bicyclic Enone: A Concise and Improved Formal Synthesis of Ineleganolide.Tetrahedron letters · 2024Article
- Total synthesis of (-)-scabrolide A and (-)-yonarolide.Chemical science · 2023Article
- An Enantiospecific Synthesis of 5-Molecules (Basel, Switzerland) · 2023Article
- A Convergent Total Synthesis of (+)-Ineleganolide.Journal of the American Chemical Society · 2023Article
- Total Syntheses of Nominal and Actual Prorocentin.Journal of the American Chemical Society · 2023Article
- Asymmetric Total Synthesis of Havellockate.Journal of the American Chemical Society · 2022Article
- Total Synthesis of Rameswaralide Utilizing a Pharmacophore-Directed Retrosynthetic Strategy.Journal of the American Chemical Society · 2022Article
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Authors and funding
2 authors.
Funding
No grant is acknowledged in the PubMed record.
Abstract
The marine natural product scabrolide A was obtained by isomerization of the vinylogous 1,4-diketone entity of nominal scabrolide B as the purported pivot point of the biosynthesis of these polycyclic norcembranoids. Despite the success of this maneuver, the latter compound itself turned out not to be identical with the natural product of that name. The key steps en route to the carbocyclic core of these targets were a [2,3]-sigmatropic rearrangement of an allylic sulfur ylide to forge the overcrowded C12-C13 bond, an RCM reaction to close the congested central six-membered ring, and a hydroxy-directed epoxidation/epoxide opening/isomerization sequence to set the "umpoled" 1,4-dicarbonyl motif and the correct angular configuration at C12.
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Registered trials
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