Scope and applications of 2,3-oxidative aryl rearrangements for the synthesis of isoflavone natural products
- The reaction of flavanones with hypervalent iodine reagents was investigated with a view to the synthesis of naturally occurring isoflavones. In contrast to several previous reports in the literature, we did not observe the formation of any benzofurans via a ring contraction pathway, but could isolate only isoflavones, resulting from an oxidative 2,3-aryl rearrangement, and flavones, resulting from an oxidation of the flavanones. Although the 2,3-oxidative rearrangement allows a synthetically useful approach toward some isoflavone natural products due to the convenient accessibility of the required starting materials, the overall synthetic utility and generality of the reaction appear to be more limited than previous literature reports suggest.
| Author details: | George KwesigaORCiDGND, Eric SperlichORCiDGND, Bernd SchmidtORCiDGND |
|---|---|
| DOI: | https://doi.org/10.1021/acs.joc.1c01375 |
| ISSN: | 0022-3263 |
| ISSN: | 1520-6904 |
| Pubmed ID: | https://pubmed.ncbi.nlm.nih.gov/34313125 |
| Title of parent work (English): | The journal of organic chemistry |
| Publisher: | American Chemical Society |
| Place of publishing: | Washington |
| Publication type: | Article |
| Language: | English |
| Date of first publication: | 2021/07/27 |
| Publication year: | 2021 |
| Release date: | 2022/11/14 |
| Volume: | 86 |
| Issue: | 15 |
| Number of pages: | 14 |
| First page: | 10699 |
| Last Page: | 10712 |
| Funding institution: | German Academic Exchange Service (DAAD)Deutscher Akademischer Austausch Dienst (DAAD) [57381412] |
| Organizational units: | Mathematisch-Naturwissenschaftliche Fakultät / Institut für Chemie |
| DDC classification: | 5 Naturwissenschaften und Mathematik / 54 Chemie / 540 Chemie und zugeordnete Wissenschaften |
| 6 Technik, Medizin, angewandte Wissenschaften / 61 Medizin und Gesundheit / 610 Medizin und Gesundheit | |
| Peer review: | Referiert |
