Studies toward the total synthesis of arylnaphthalene lignans via a Photo-Dehydro-Diels-Alder (PDDA) reaction
- An efficient method for the preparation of arylnaphthalene lignans (ANLs) was developed, which is based on thePhoto-Dehydro-DIELS-ALDER(PDDA) reaction. While intermolecular PDDA reactions turned out to be inefficient, theintramolecular variant using suberic acid as tether linking two aryl propiolic esters smoothly provided naphthalenophanes. Theirradiations were performed with a previously developed annular continuous-flow reactor and UVB lamps. In this way, the naturalproducts Alashinol D, Taiwanin C, and an unnamed ANL could be prepared.
| Author details: | Pablo WessigORCiDGND, Dominik Badetko, Maciej CzarneckiORCiDGND, Lukas Wichterich, Peter Schmidt, Cosima Brudy, Eric SperlichORCiDGND, Alexandra Kelling |
|---|---|
| DOI: | https://doi.org/10.1021/acs.joc.2c00195 |
| ISSN: | 0022-3263 |
| ISSN: | 1520-6904 |
| Pubmed ID: | https://pubmed.ncbi.nlm.nih.gov/35388702 |
| 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: | 2022/04/07 |
| Publication year: | 2022 |
| Release date: | 2023/01/23 |
| Volume: | 87 |
| Issue: | 9 |
| Number of pages: | 12 |
| First page: | 5904 |
| Last Page: | 5915 |
| Funding institution: | Deutsche Forschungsgemeinschaft [We1850-12/1] |
| 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 |
