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The first total synthesis of (±)-annosqualine by means of oxidative enamide-phenol coupling: pronounced effect of phenoxide formation on the phenol oxidation mechanism
| Content Provider | Semantic Scholar |
|---|---|
| Author | Shigehisa, Hiroki Takayama, Jun Honda, Toshio |
| Copyright Year | 2006 |
| Abstract | Abstract The first total synthesis of a spiro-isoquinoline alkaloid, (±)-annosqualine, was established by employing an enamide–phenol coupling of a 1-methylene-1,2,3,4-tetrahydroisoquinoline derivative with a hypervalent iodine reagent, where the formation of the phenoxide was recognized to be an essential step for the reaction of the phenolic hydroxyl group with the hypervalent iodine reagent leading to the formation of the desired product. |
| Starting Page | 7301 |
| Ending Page | 7306 |
| Page Count | 6 |
| File Format | PDF HTM / HTML |
| DOI | 10.1016/j.tetlet.2006.08.028 |
| Volume Number | 47 |
| Alternate Webpage(s) | https://polaris.hoshi.ac.jp/kyoshitsu/keitai/open%20resarch%20HP%20%E6%9C%80%E6%96%B0%20-%20%E3%82%B3%E3%83%94%E3%83%BC/5%20Annosqualine-1.pdf |
| Alternate Webpage(s) | https://doi.org/10.1016/j.tetlet.2006.08.028 |
| Language | English |
| Access Restriction | Open |
| Content Type | Text |
| Resource Type | Article |
