RESUMEN
The first total synthesis of (-)-crinipellin A is described. The tetraquinane core skeleton of crinipellin A was assembled through the tandem [2 + 3] cycloaddition reaction of an allenyl diazo substrate containing a cyclopentane ring in a single operation. The absolute stereochemistry was confirmed through the total synthesis.
Asunto(s)
Ciclopentanos/química , Diterpenos/síntesis química , Metano/análogos & derivados , Compuestos Azo/química , Reacción de Cicloadición , Diterpenos/química , Metano/química , Conformación Molecular , EstereoisomerismoRESUMEN
Total synthesis of ceratopicanol (1) was achieved with a tandem cycloaddition reaction of allenyl diazo compound 6 via a trimethylenemethane (TMM) diyl intermediate. The TMM diyl mediated [2+3] cycloaddition reaction furnished the consecutive quaternary carbon centers and showed an unusual diastereoselectivity.
Asunto(s)
Compuestos Policíclicos/síntesis química , Compuestos Azo/química , Reacción de Cicloadición , Metano/análogos & derivados , Metano/química , Compuestos Policíclicos/química , EstereoisomerismoRESUMEN
A tandem reaction strategy for forming triquinanes from linear allenyl diazo compounds through an intramolecular 1,3-dipolar cycloaddition reaction of an allenyl diazo group that generates a trimethylenemethane (TMM) diyl followed by an intramolecular [2 + 3] TMM diyl cycloaddition reaction has been developed. The new tandem cycloaddition reaction is readily applicable to the synthesis of complex molecules with high versatility and efficiency.
Asunto(s)
Compuestos Azo/química , Hidrocarburos Aromáticos con Puentes/síntesis química , Metano/análogos & derivados , Sesquiterpenos/síntesis química , Hidrocarburos Aromáticos con Puentes/química , Ciclización , Metano/química , Estructura Molecular , Sesquiterpenos/química , EstereoisomerismoRESUMEN
A series of Incentrom A analogs that inhibit the chromosome segregation process in yeast were synthesized and tested for their effects on chromosome stability and cell proliferation. Pharmacophore and structure-activity relationship of Incentrom A for the anti-yeast activity were established.
