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Carbotriciclización carbonilativa iniciada por silicio y [2+2+2+1] cicloadición de enediinas catalizadas por
Bibia Bennacer1, Masaki Fujiwara, Seung-Yub Lee
1Department of Chemistry, State University of New York at Stony Brook, Stony Brook, New York 11794-3400, USA.
Journal of the American Chemical Society
|December 15, 2005
Resumen
Los investigadores desarrollaron dos nuevas reacciones para sintetizar compuestos tricíclicos 5-7-5 fundidos a partir de enediinas. Estos procesos de carbotriciclización carbonilativa en cascada iniciada por el silicio (CO-SiCaT) y de cicloadición intramolecular ofrecen rutas eficientes a moléculas policíclicas complejas.
Área de la Ciencia:
- Química orgánica es la química orgánica.
- Química sintética de la química sintética.
- La catálisis es la catálisis.
Sus antecedentes:
- Los compuestos de enediyne son precursores versátiles en la síntesis orgánica.
- El desarrollo de métodos eficientes para la construcción de estructuras policíclicas complejas sigue siendo un desafío clave.
Objetivo del estudio:
- Introducir nuevas rutas sintéticas para los compuestos tricíclicos 5-7-5 fusionados.
- Para explorar la carbotriciclización carbonilativa en cascada iniciada por silicio (CO-SiCaT) y las reacciones de cicloadición intramolecular.
Principales métodos:
- Reacción catalizada por el rodio de dodec-11-ene-1,6-diynes con hidrosilano y CO.
- Cicloadición intramolecular [2+2+2+1] de enediinas y diinales con CO.
Principales resultados:
- Se obtuvieron excelentes rendimientos de productos tricíclicos fusionados 5-7-5 (5-oxo-1,3a,4,5,7,9-hexahidro-3H-cyclopenta[e]azulenes) a través del proceso CO-SiCaT.
- La cicloadición intramolecular [2+2+2+1] también produjo con éxito los productos tricíclicos fusionados 5-7-5.
- Las reacciones se aplicaron a la triciclización de undeca-5,10-diyn-1-als, dando como resultado productos con una porción de lactona de siete miembros.
Conclusiones:
- Se han descubierto dos vías distintas y eficientes para sintetizar complejos sistemas tricíclicos fusionados 5-7-5 a partir de precursores lineales.
- Estas reacciones permiten la rápida construcción de compuestos policíclicos, ofreciendo rutas innovadoras para la síntesis de productos naturales y no naturales.
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