ArticleJournal of the American Chemical Society2018
Total Synthesis of Salimabromide: A Tetracyclic Polyketide from a Marine Myxobacterium.
Article in Journal of the American Chemical Society, 2018. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 9 papers.
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Who cites it
9 citing papers in PubMed.
- Strategic Applications of Single-Atom Skeletal Editing in Natural Product Synthesis.Journal of the American Chemical Society · 2026Review
- Stereospecific Synthesis of Cyclobutanones and Spirohexanones via Formal [3 + 1] Cycloaddition of Cyclopropanones with Sulfur Ylides.Organic letters · 2025Article
- 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
- Highlights from the 57th Bürgenstock Conference on Stereochemistry 2024.Chemical science · 2024Article
- Recent Advances in the Synthesis of 3,4-Dihydropyran-2-Ones Organocatalyzed byMolecules (Basel, Switzerland) · 2023Review
- Naturally Occurring Organohalogen Compounds-A Comprehensive Review.Progress in the chemistry of organic natural products · 2023Review
- Total Synthesis of the Dihydrooxepine-Spiroisoxazoline Natural Product Psammaplysin A.Journal of the American Chemical Society · 2022Article
- Synthesis of Vicinal Quaternary All-Carbon Centers via Acid-catalyzed Cycloisomerization of Neopentylic Epoxides.Organic letters · 2020Article
- Ring-Expansion Approaches for the Total Synthesis of Salimabromide.Tetrahedron · 2019Article
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Authors and funding
4 authors.
Funding
Abstract
Salimabromide is an antibiotic polyketide that was previously isolated from the obligate marine myxobacterium Enhygromyxa salina, and its densely functionalized and conformationally rigid tetracyclic framework is unprecedented in nature. Herein we report the first chemical synthesis of the target structure by employing a series of well-orchestrated, robust transformations, highlighted by an acid-promoted, powerful Wagner-Meerwein rearrangement/Friedel-Crafts cyclization sequence to forge the two adjacent quaternary carbon centers embedded in the tetrahydronaphthalene. A high-yielding ketiminium mediated [2+2]-cycloaddition was also utilized for the simultaneous construction of the remaining three stereocenters.
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.