Enantioselective total synthesis of pinnaic acid and halichlorine
Xu, S; Unabara, D; Uemura, D; Arimoto, H
| HERO ID | 2900159 |
|---|---|
| In Press | No |
| Year | 2014 |
| Title | Enantioselective total synthesis of pinnaic acid and halichlorine |
| Authors | Xu, S; Unabara, D; Uemura, D; Arimoto, H |
| Journal | Chemistry - An Asian Journal |
| Volume | 9 |
| Issue | 1 |
| Page Numbers | 367-375 |
| Abstract | The enantioselective total synthesis of the bioactive marine natural products pinnaic acid and halichlorine is reported in detail. Our total synthesis features the construction of the five-membered ring and C9 and C13 stereogenic centers through a palladium-catalyzed trimethylenemethane [3+2] cyclization; the installation of the nitrogen atom through a regioselective Beckmann rearrangement of a poorly reactive ketone; the stereoselective cyclization of the spiro ring through a four-step, one-pot hydrogenation-cyclization; and efficient connection of the sterically hindered lower chain through a reduced-pressure cross olefin metathesis reaction. |
| Doi | 10.1002/asia.201301248 |
| Pmid | 24136879 |
| Is Certified Translation | No |
| Dupe Override | No |
| Is Public | Yes |
| Language Text | English |