ArticleAngewandte Chemie (International ed. in English)2020
Total Synthesis of Pyrolaside B: Phenol Trimerization through Sequenced Oxidative C-C and C-O Coupling.
Article in Angewandte Chemie (International ed. in English), 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 5 papers.
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5 citing papers in PubMed.
- Photocatalytic Cross-Coupling of Phenols and Heteroaryl Halides With Machine Learning-Guided Reaction Prediction.Angewandte Chemie (International ed. in English) · 2026Article
- Recent advances in oxidative phenol coupling for the total synthesis of natural products.Natural product reports · 2024Review
- Direct conversion of lignin to functionalized diaryl ethers via oxidative cross-coupling.Nature communications · 2023Article
- Catalytic Oxidative Coupling of Phenols and Related Compounds.ACS catalysis · 2022Article
- Oxidative dehydrogenative couplings of alkenyl phenols.Organic & biomolecular chemistry · 2021Review
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Abstract
A facile method to oxidatively trimerize phenols using a catalytic aerobic copper system is described. The mechanism of this transformation was probed, yielding insight that enabled cross-coupling trimerizations. With this method, the natural product pyrolaside B was synthesized for the first time. The key strategy used for this novel synthesis is the facile one-step construction of a spiroketal trimer intermediate, which can be selectively reduced to give the natural product framework without recourse to stepwise Ullmann- and Suzuki-type couplings. As a result, pyrolaside B can be obtained expeditiously in five steps and 16 % overall yield. Three other analogues were synthesized, thus highlighting the utility of the method, which provides new accessibility to this area of chemical space. A novel xanthene was also synthesized through controlled Lewis acid promoted rearrangement of a spiroketal trimer.
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