Phaseolinone
菜豆壳孢酮Chemical Name: 3(S),4(R)-Epoxy-6(R)-hydroxy-3-[2-(hydroxymethyl)oxiran-2-yl]-4a(S),5(R)-dimethyl-2,3,4,4a,5,6,7,8-octahydronaphthalen-2-one
CAS No. 85431-61-4
项目整合开发状态: Preclinical
项目研究机构: Inst. Physical Chemical Res. (RIKEN) (Originator)
合成路线:The reaction of tert-butyldimethylsilyloxy-sporogen-AOI (I) with phenylselenyl trifluoroacetate (II) gives the adduct (IIIa-b),which is treated first with MCPBA and then with K2CO3 in methanol to yield compound (IV).The Sharpless asymmetric epoxidation of (IV) with D-(-)-diisopropyl tartrate,Ti(OiPr)4 and tBu-OOH affords the mixture of diepoxides (Va)+(Vb),which is silylated with TBDMSCl and imidazole to the disilylated mixture of diepoxides (VIa)+(VIb).Finally this mixture is separated by column chromatography,and the desired diastereomer submitted to desilylation with TBAF to furnish the target compound.
📌 参考资料/链接：
参考文献标题:Synthesis of oxygenated morphilanes,gigantone phomenone and phaseolinone,phytotoxins from pathogenic fungi
文献作者:Kitahara,T.; Kurata,H.; Mori,K.; Kiyoto,H.
参考来源:Tetrahedron 1991,1649-54
📄 详细内容
合成路线:The reaction of tert-butyldimethylsilyloxy-sporogen-AOI (I) with phenylselenyl trifluoroacetate (II) gives the adduct (IIIa-b),which is treated first with MCPBA and then with K2CO3 in methanol to yield compound (IV).The Sharpless asymmetric epoxidation of (IV) with D-(-)-diisopropyl tartrate,Ti(OiPr)4 and tBu-OOH affords the mixture of diepoxides (Va)+(Vb),which is silylated with TBDMSCl and imidazole to the disilylated mixture of diepoxides (VIa)+(VIb).Finally this mixture is separated by column chromatography,and the desired diastereomer submitted to desilylation with TBAF to furnish the target compound.
参考文献标题:Antileishmanial agents
文献作者:Bhadra,R.
参考来源:Drugs Fut 1993,18(5),451
产品链接: CAS No. 85431-61-4››