Palladium-mediated C-N, C-C, and C-O functionalization of azolopyrimidines: a new total synthesis of variolin B
A new total synthesis of the alkaloid variolin B is achieved by a selective and sequential palladium-mediated functionalization of a trihalo-substituted pyrido[30 ,20 :4,5]pyrrolo[1,2-c]pyrimidine. This intermediate is obtained by a new heterocyclization reaction between an appropriate bromomethyl a...
| Autores: | , , , , |
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| Tipo de recurso: | artículo |
| Fecha de publicación: | 2008 |
| País: | España |
| Institución: | Universidad de Alcalá (UAH) |
| Repositorio: | e_Buah Biblioteca Digital Universidad de Alcalá |
| Idioma: | inglés |
| OAI Identifier: | oai:ebuah.uah.es:10017/2653 |
| Acceso en línea: | http://hdl.handle.net/10017/2653 https://dx.doi.org/10.1016/j.tetlet.2008.04.063 |
| Access Level: | acceso abierto |
| Palabra clave: | Variolin B Total synthesis Palladium-mediated C-N, C-C and C-O pyrido[3 ',2 ': 4,5]pyrrolo[1,2-c]pyrimidine N-tosylmethyl dichloro-formimide Sponge kirkpatrickia-varialosa Deoxyvariolin-B Bond formation Alkaloids Core Derivatives Ethers Chemistry, Organic Bioquímica Ciencia Biochemistry Science |
| Sumario: | A new total synthesis of the alkaloid variolin B is achieved by a selective and sequential palladium-mediated functionalization of a trihalo-substituted pyrido[30 ,20 :4,5]pyrrolo[1,2-c]pyrimidine. This intermediate is obtained by a new heterocyclization reaction between an appropriate bromomethyl azaindole and N-tosylmethyl dichloroformimide. The methodology may be effective for the synthesis of some analogs by substitution on the relatively unexplored C4 and C9 positions of the alkaloid. |
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