新产品编号:14747
Chemical Name: 5-Hydroxy-3,4,7-triphenyl-2,6-benzofurandione
CAS No. 114590-95-3
项目整合开发状态: Biological Testing
项目研究机构: University of Nottingham (Originator)
合成路线:Addition of benzylmagnesium chloride to O-(trimethylsilyl)cyanohydrin (II) (obtained from phenylacetaldehyde (I) and Me3SiCN),led to benzylacyloin (III).Esterification with ethyl oxalyl chloride (IV) in the presence of Et3N afforded oxalate (V),which was cyclized with DBU in cold DMF to provide dihydrogrevillin (VI).This was methylated with ethereal diazomethane to give ether (VII),and then brominated in AcOH.Elimination of the resulting bromide (VIII) by treatment with DBU produced (IX),which was demethylated with BBr3 to afford grevillin (X).This compound was isomerized with NaOEt in EtOH to produce terphenyl quinone (XI).Finally,Perkin reaction with phenylacetic acid (XII),followed by treatment with HBr furnished the title compound.
📌 参考资料/链接：
参考文献标题:Synthesis of grevillins and their biogenetic interrelationship with terphenylquinones,xylerythrins and pulvinic acids
文献作者:Pattenden,G.; et al.
参考来源:Tetrahedron Lett 1987,28(4),4749
📄 详细内容
合成路线:Addition of benzylmagnesium chloride to O-(trimethylsilyl)cyanohydrin (II) (obtained from phenylacetaldehyde (I) and Me3SiCN),led to benzylacyloin (III).Esterification with ethyl oxalyl chloride (IV) in the presence of Et3N afforded oxalate (V),which was cyclized with DBU in cold DMF to provide dihydrogrevillin (VI).This was methylated with ethereal diazomethane to give ether (VII),and then brominated in AcOH.Elimination of the resulting bromide (VIII) by treatment with DBU produced (IX),which was demethylated with BBr3 to afford grevillin (X).This compound was isomerized with NaOEt in EtOH to produce terphenyl quinone (XI).Finally,Perkin reaction with phenylacetic acid (XII),followed by treatment with HBr furnished the title compound.
参考文献标题:Synthesis of grevillins,novel pyrandione pigments of fungi.Biogenetic ibnterrelationships between grevillins,pulvinic acids,terphenylquinones and xylerythrins
文献作者:Pattenden,G.; et al.
参考来源:J Chem Soc - Perkins Trans I 1991,2363