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Total synthesis of polyprenoid natural products via Pd(0)-catalyzed oligomerizations
| Content Provider | Semantic Scholar |
|---|---|
| Author | Keinan, Ehud Eren, Doron |
| Copyright Year | 1988 |
| Abstract | A general methodology for highly regio- and stereoselective Pd(0)-catalyzed, stepwise allylic coupling of bifunctional monomers was developed, representing a practical approach for total synthesis of naturally occurring polyprenoids. As an example, the total synthesis of the cardiovascular agent, ubiquinone 10 (coenzyme Q1O), as well as shorter ubiquinones was carried out via selective coupling of monomers, easily derived from geraniol, that contain either one or two reacting functional end groups. One of these functionalities is a latent allylic electrophile that is activated by the Pd(0) catalyst and the other is a latent nucleophile activated by an appropriate base. After achieving the desired decaprenyl carbon skeleton of Qlo, the synthesis was completed by removal of the activating groups: methyl ester was deleted via a highly efficient demethoxycarbonylation procedure involving 4-aminothiophenol and catalytic amounts of cesium carbonate, and the allylic sulfones by Pd(0)-catalyzed allylic reduction. Finally, oxidation of the aromatic ring to quinone affords ubiquinone-10. |
| Starting Page | 89 |
| Ending Page | 98 |
| Page Count | 10 |
| File Format | PDF HTM / HTML |
| DOI | 10.1351/pac198860010089 |
| Volume Number | 60 |
| Alternate Webpage(s) | http://old.iupac.org/publications/pac/1988/pdf/6001x0089.pdf |
| Alternate Webpage(s) | https://doi.org/10.1351/pac198860010089 |
| Language | English |
| Access Restriction | Open |
| Content Type | Text |
| Resource Type | Article |
