RESUMO
The first total synthesis of monosporascone is presented. The five-step synthesis developed includes a silver acetylide-acid chloride coupling, domino Diels-Alder-retro-Diels-Alder reaction, and an intramolecular Friedel-Crafts acylation, and provides the natural product in 57% yield overall. Selective reduction of monosporascone also afforded the related metabolite dihydromonosporascone.
Assuntos
Produtos Biológicos/síntese química , Furanos/química , Compostos Heterocíclicos/síntese química , Naftoquinonas/química , Acilação , Espectroscopia de Ressonância Magnética , Espectrometria de Massas , Estrutura MolecularRESUMO
An improved synthesis of the anti-inflammatory natural product antrocamphin A (2), involving a key Castro-Stephens reaction, is presented, along with the first total synthesis of its congener antrocamphin B (3). Approaches towards the more complex co-metabolite antrodioxolanone (4) were unsuccessful, but a samarium diiodide-mediated pinacol coupling of antrocamphin B did provide the chiral epimers (51). Antrocamphin A (2) inhibits Tumour Necrosis Factor (TNF) reporter gene expression, but its development as an anti-inflammatory agent may be limited by cytotoxicity.
Assuntos
Alcinos/farmacologia , Anisóis/farmacologia , Antrodia/química , Produtos Biológicos/farmacologia , Receptores do Fator de Necrose Tumoral/antagonistas & inibidores , Alcinos/química , Alcinos/metabolismo , Anisóis/química , Anisóis/metabolismo , Antrodia/metabolismo , Produtos Biológicos/química , Produtos Biológicos/metabolismo , Morte Celular/efeitos dos fármacos , Linhagem Celular , Relação Dose-Resposta a Droga , Humanos , Estrutura Molecular , Receptores do Fator de Necrose Tumoral/genética , Relação Estrutura-AtividadeRESUMO
The title compound, which was reported to be a constituent of the fruiting body of the fungus Antrodia camphorata, has been synthesized. The reactivity and spectroscopic properties of the synthetic material do not match those of the natural product. There is currently insufficient information for a definitive structural reassignment.
