Pd-Catalyzed arylation reactions with phenol diazonium salts application in the synthesis of diarylheptanoids
- The first total synthesis of the natural product (3S,7R)-5,6-dehydro-de-O-methyl centrolobine and various analogues is reported, using a highly regio- and diastereoselective Mizoroki-Heck reaction of phenol diazonium salts and enantiopure dihydropyrans. The assigned relative configuration was confirmed by single-crystal X-ray structure analysis, but a revision of the absolute configuration is proposed based on polarimetric measurement.
| Author details: | Bernd SchmidtORCiDGND, Frank Hölter, Alexandra Kelling, Uwe SchildeORCiDGND |
|---|---|
| DOI: | https://doi.org/10.1021/jo2002787 |
| ISSN: | 0022-3263 |
| ISSN: | 1520-6904 |
| Title of parent work (English): | The journal of organic chemistry |
| Publisher: | American Chemical Society |
| Place of publishing: | Washington |
| Publication type: | Article |
| Language: | English |
| Year of first publication: | 2011 |
| Publication year: | 2011 |
| Release date: | 2017/03/26 |
| Volume: | 76 |
| Issue: | 9 |
| Number of pages: | 9 |
| First page: | 3357 |
| Last Page: | 3365 |
| Funding institution: | Deutsche Forschungsgemeinschaft [Schm 1095/6-1] |
| Organizational units: | Mathematisch-Naturwissenschaftliche Fakultät / Institut für Biochemie und Biologie |
| Peer review: | Referiert |
