Concise and very efficient synthesis of the N-methylwelwistatin tetracyclic core based on an anionic domino process
An efficient synthesis of the N-methylwelwistatin tetracyclic core in only two steps from Kornfeld's ketone is described, whose key transformation involves the generation of a fused bicyclo[4.3.1]decane ring system through a one-pot sequence comprising a Michael-intramolecular aldolization anio...
| Autores: | , , |
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| Tipo de recurso: | artículo |
| Fecha de publicación: | 2010 |
| País: | España |
| Institución: | Universidad Complutense de Madrid (UCM) |
| Repositorio: | Docta Complutense |
| Idioma: | inglés |
| OAI Identifier: | oai:docta.ucm.es:20.500.14352/128965 |
| Acceso en línea: | https://hdl.handle.net/20.500.14352/128965 |
| Access Level: | acceso abierto |
| Palabra clave: | 615:54 615.31 661.185 N-methylwelwistatin Domino process Synthesis Química farmaceútica Química orgánica (Farmacia) 2306.90 Química de Productos Naturales Orgánicos 2306 Química Orgánica |
| Sumario: | An efficient synthesis of the N-methylwelwistatin tetracyclic core in only two steps from Kornfeld's ketone is described, whose key transformation involves the generation of a fused bicyclo[4.3.1]decane ring system through a one-pot sequence comprising a Michael-intramolecular aldolization anionic domino process and a DBU-promoted hydrolysis of the N-pivaloyl protecting group. Besides providing the most efficient synthesis of the welwistatin core to date, this method has the advantage of installing an oxygenated function at the welwistatin D ring. |
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