RESUMEN
Three members of the cannabinoid class, cannabinol, cannabinol methyl ether, and cannabinodiol, were synthesized using a microwave-mediated [2 + 2 + 2] cyclotrimerization reaction as the key step. This approach provides a high level of synthetic flexibility allowing for the facile synthesis of cannabinoid analogues.
Asunto(s)
Cannabinoides/síntesis química , Alquinos/química , Cannabinoides/química , Ciclización , Nitrilos/químicaRESUMEN
A concise synthesis of phenanthridines via a microwave-assisted [2+2+2] cyclotrimerization reaction has been developed.
Asunto(s)
Fenantridinas/síntesis química , Ciclización , Microondas , Estructura Molecular , Fenantridinas/química , Fenantridinas/efectos de la radiación , EstereoisomerismoRESUMEN
Rapid and efficient [2 + 2 + 2] cyclotrimerization reactions were discovered through the application of microwave irradiation in conjunction with a Ni(CO)(2)(PPh(3))(2) catalyst. This enables the facile construction of highly substituted indane, isoindoline, and tetraline core structures. The developed microwave-mediated Ni-catalyzed cyclotrimerization reaction was employed as the key step in a concise synthesis of the isoquinoline natural product illudinine. This represents the first example of a Ni-catalyzed cyclotrimerization reaction in total synthesis.
Asunto(s)
Microondas , Níquel/química , Níquel/efectos de la radiación , Compuestos Organometálicos/química , Compuestos Organometálicos/efectos de la radiación , Sesquiterpenos/síntesis química , Sesquiterpenos/efectos de la radiación , Catálisis , Ciclización , Estructura Molecular , Sesquiterpenos/química , EstereoisomerismoRESUMEN
A new facile approach toward natural and unnatural indanones has been developed, featuring a solid-supported [2+2+2] cyclotrimerization as the key step. This strategy has been applied to the chemo- and regioselective assembly of indanone arrays and to the total synthesis of a recently isolated indanone marine natural product.