ArticleNature communications2024
Late-stage benzenoid-to-troponoid skeletal modification of the cephalotanes exemplified by the total synthesis of harringtonolide.
Article in Nature communications, 2024. 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.
- Strategic Applications of Single-Atom Skeletal Editing in Natural Product Synthesis.Journal of the American Chemical Society · 2026Review
- Total syntheses of (+)-dalesconols A and B enabled by triple-relayed remote chirality transfer.Nature communications · 2026Article
- A difluorocarbene-triggered annulation/ring expansion cascadeChemical science · 2026Article
- Liquid-Phase Peptide Synthesis of Tropolone-Peptide Hybrid Antimalarials.Organic letters · 2026Article
- Ring contraction and ring expansion reactions in terpenoid biosynthesis and their application to total synthesis.Beilstein journal of organic chemistry · 2026Review
- Harnessing Photochemistry in Natural Product Synthesis: From Strategy to Applications.Journal of natural products · 2025Review
- Skeletal Editing Strategies Driven by Total Synthesis.Accounts of chemical research · 2025Article
- Visible-light-mediated site-selective C(spChemical science · 2025Article
- Asymmetric total synthesis of benzenoid cephalotane-type diterpenoids through a cascade C(spNature communications · 2025Article
- Advancing Total Synthesis Through Skeletal Editing.Accounts of chemical research · 2025Article
- Unified Total Synthesis of Benzenoid and TroponoidJACS Au · 2025Article
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Authors and funding
7 authors.
Funding
Abstract
Skeletal modifications enable elegant and rapid access to various derivatives of a compound that would otherwise be difficult to prepare. They are therefore a powerful tool, especially in the synthesis of natural products or drug discovery, to explore different natural products or to improve the properties of a drug candidate starting from a common intermediate. Inspired by the biosynthesis of the cephalotane natural products, we report here a single-atom insertion into the framework of the benzenoid subfamily, providing access to the troponoid congeners - representing the reverse of the proposed biosynthesis (i.e., a contra-biosynthesis approach). Computational evaluation of our designed transformation prompted us to investigate a Büchner-Curtius-Schlotterbeck reaction of a p-quinol methylether, which ultimately results in the synthesis of harringtonolide in two steps from cephanolide A, which we had previously prepared. Additional computational studies reveal that unconventional selectivity outcomes are driven by the choice of a Lewis acid and the nucleophile, which should inform further developments of these types of reactions.
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