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An Asymmetric Synthesis of 1,2,4-Trioxane Anticancer Agents via Desymmetrization of Peroxyquinols through a Brønsted Acid Catalysis Cascade
Open accessAbstract
The desymmetrization of p-peroxyquinols using a Brønsted acid-catalyzed acetalization/oxa-Michael cascade was achieved in high yields and selectivities for a variety of aliphatic and aryl aldehydes. Mechanistic studies suggest that the reaction proceeds through a dynamic kinetic resolution of the peroxy hemiacetal intermediate. The resulting 1,2,4-trioxane products were derivatized and show potent cancer cell-growth inhibition.
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Artemisinin Resistance in Plasmodium falciparum Malaria
Dondorp, A. M., Nosten, F., Yi, P., Das, D., Phyo, A. P., Tarning, J., Lwin, K. M., Ariey, F., Hanpithakpong, W., Lee, S. J., et al. (2009) · New England Journal of Medicine · doi:10.1056/nejmoa0808859 · Cited by 3,424
Cited by
Parmar, D., Sugiono, E., Raja, S., & Rueping, M. (2014) · Chemical Reviews · doi:10.1021/cr5001496 · Cited by 2,118
Metadata
- Authors
- Rubush, D. M., Morges, M. A., Rose, B. J., Thamm, D. H., & Rovis, T.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2012-08-07
- Volume
- 134
- Issue
- 33
- Pages
- 13554-13557
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W2093546262
- Cited by
- 212
- References
- 1
- FWCI
- 12.54
- Type
- journal article
- Language
- en
- Open access
- green
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- CoChat. (2026). Citation check: An Asymmetric Synthesis of 1,2,4-Trioxane Anticancer Agents via Desymmetrization of Peroxyquinols through a Brønsted Acid Catalysis Cascade. https://app.cochat.ai/papers/10.1021/ja3052427
- The paper
- Rubush, D. M., Morges, M. A., Rose, B. J., Thamm, D. H., & Rovis, T. (2012). An Asymmetric Synthesis of 1,2,4-Trioxane Anticancer Agents via Desymmetrization of Peroxyquinols through a Brønsted Acid Catalysis Cascade. Journal of the American Chemical Society. https://doi.org/10.1021/ja3052427
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Contains information from the Semantic Scholar Academic Graph Datasets, made available under the ODC Attribution License (ODC-BY 1.0).
Semantic Scholar’s data is described in: Kinney, R., et al. (2023). The Semantic Scholar Open Data Platform. arXiv:2301.10140.