Ring-closing-metathesis-based synthesis of annellated coumarins from 8-allylcoumarins
- 8-Allylcoumarins are conveniently accessible through a microwave-promoted tandem Claisen rearrangement/Wittig olefination/cyclization sequence. They serve as a versatile platform for the annellation of five- to seven-membered rings using ring-closing olefin metathesis (RCM). Furano-, pyrano-, oxepino- and azepinocoumarins were synthesized from the same set of precursors using Ru-catalyzed double bond isomerizations and RCM in a defined order. One class of products, pyrano[2,3-f]chromene-2,8-diones, were inaccessible through direct RCM of an acrylate, but became available from the analogous allyl ether via an assisted tandem catalytic RCM/allylic oxidation sequence.
| Author details: | Christiane SchultzeGND, Bernd SchmidtORCiDGND |
|---|---|
| DOI: | https://doi.org/10.3762/bjoc.14.278 |
| ISSN: | 1860-5397 |
| Pubmed ID: | https://pubmed.ncbi.nlm.nih.gov/30591822 |
| Title of parent work (English): | Beilstein journal of organic chemistry |
| Publisher: | Beilstein-Institut zur Förderung der Chemischen Wissenschaften |
| Place of publishing: | Frankfurt, Main |
| Publication type: | Article |
| Language: | English |
| Date of first publication: | 2018/12/05 |
| Publication year: | 2018 |
| Release date: | 2020/12/15 |
| Tag: | coumarins; heterocycles; isomerization; olefin metathesis; ruthenium |
| Volume: | 14 |
| Number of pages: | 8 |
| First page: | 2991 |
| Last Page: | 2998 |
| Organizational units: | Mathematisch-Naturwissenschaftliche Fakultät / Institut für Chemie |
| DDC classification: | 5 Naturwissenschaften und Mathematik / 54 Chemie / 540 Chemie und zugeordnete Wissenschaften |
| Peer review: | Referiert |
| Publishing method: | Open Access / Gold Open-Access |
| DOAJ gelistet | |
| License (German): |  CC-BY - Namensnennung 4.0 International |
