ArticleJournal of the American Chemical Society2024
Concise Total Syntheses of (
Article in Journal of the American Chemical Society, 2024. 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.
- Article
- Total syntheses of (+)-dalesconols A and B enabled by triple-relayed remote chirality transfer.Nature communications · 2026Article
- A Concise Total Synthesis of (+)-Pedrolide.Journal of the American Chemical Society · 2026Article
- Total Synthesis of (-)-Psathyrin A Enabled by Radical Cyclization.Journal of the American Chemical Society · 2025Article
- [2,3]-Sigmatropic rearrangement with [1.1.1]propellane.Nature communications · 2025Article
- Total Synthesis of (-)-Illisimonin A Enabled by Pattern Recognition and Olefin Transposition.Journal of the American Chemical Society · 2025Article
- Avoidance of Secondary Carbocations, Unusual Deprotonation, and Nonstatistical Dynamic Effects in the Cyclization Mechanism of Tetraisoquinane.Journal of the American Chemical Society · 2025Article
- Advancing Total Synthesis Through Skeletal Editing.Accounts of chemical research · 2025Article
- Molecular Complexity-Inspired Synthetic Strategies toward the Calyciphylline A-TypeJournal of the American Chemical Society · 2024Article
Corrections and comments
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Authors and funding
4 authors.
Funding
Abstract
Herein, we report concise total syntheses of diterpene natural products (-)-crinipellins A and B with a tetraquinane skeleton, three adjacent all-carbon quaternary centers, and multiple oxygenated and labile functional groups. Our synthesis features a convergent Kozikowski β-alkylation to unite two readily available building blocks with all the required carbon atoms, an intramolecular photochemical [2 + 2] cycloaddition to install three challenging and adjacent all-carbon quaternary centers and a 5-6-4-5 tetracyclic skeleton, and a controlled Cargill rearrangement to rearrange the 5-6-4-5 tetracyclic skeleton to the desired tetraquinane skeleton. These strategically enabling transformations allowed us to complete total syntheses of (-)-crinipellins A and B in 12 and 13 steps, respectively. The results of quantum chemical computations revealed that the Bronsted acid-catalyzed Cargill rearrangements likely involve stepwise paths to products and the AlR
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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 Socratic graph.