Pericyclic Cascade toward Isochromenes: Application to the Synthesis of Alkaloid Benzosimuline
The synthesis of biologically active alkaloid benzosimuline, isolated from the shrub Zanthoxylum simulans, is reported. Key transformation involves an oxa-6π electrocyclic ring-opening/hetero-Diels-Alder pericyclic cascade. Although the last aromatization step proved to be cumbersome, this work unfo...
| Autores: | , , |
|---|---|
| Formato: | artículo |
| Estado: | Versión publicada |
| Fecha de publicación: | 2016 |
| País: | Argentina |
| Recursos: | Consejo Nacional de Investigaciones Científicas y Técnicas |
| Repositorio: | CONICET Digital (CONICET) |
| Idioma: | inglés |
| OAI Identifier: | oai:ri.conicet.gov.ar:11336/52692 |
| Acesso em linha: | http://hdl.handle.net/11336/52692 |
| Access Level: | acceso abierto |
| Palavra-chave: | DOMINO REACTIONS ALKALOIDS HETERO DIELS-ALDER PERICYCLIC REACTIONS https://purl.org/becyt/ford/1.4 https://purl.org/becyt/ford/1 |
| Resumo: | The synthesis of biologically active alkaloid benzosimuline, isolated from the shrub Zanthoxylum simulans, is reported. Key transformation involves an oxa-6π electrocyclic ring-opening/hetero-Diels-Alder pericyclic cascade. Although the last aromatization step proved to be cumbersome, this work unfolds a unique route to access interesting molecules from simple precursors. |
|---|