新产品编号:2493741
Chemical Name: (1R,4S,5R,8R)-8-(Benzyloxy)-4,8-dimethyl-4-(phenylsulfonylmethyl)-2,3-dioxabicyclo[3.3.1]nonane
项目整合开发状态: Preclinical
项目研究机构: Johns Hopkins University (Originator), Yeda (Originator)
合成路线:(R)-(+)-Limonene (I) is subjected to a free-radical sequential thiol-olefin cooxygenation in the presence of O2,thiophenol and di-tert-butyl peroxalate (DBPO) to furnish the sulfenyl endoperoxide (II) as a mixture of diastereoisomers.Chemoselective reduction of the hydroperoxide function of (II) with PPh3 yields alcohol (III).After oxidation of the sulfenyl group of (III) to the corresponding sulfone with mCPBA,the required isomer (IV) is isolated employing medium-pressure liquid chromatography.Finally,treatment of alcohol (IV) with phenyldiazomethane in the presence of trifluoromethanesulfonic acid gives rise to the O-benzylated derivative (1,2).
📌 参考资料/链接：
参考文献标题:2,3-Dioxabicyclo[3.3.1]nonane derivs.and antimalarial pharmaceutical compsns.comprising them
文献作者:Posner,G.H.; Bachi,M.; Korshin,E.(Johns Hopkins University; Yeda Research & Development Co.Ltd.)
参考来源:US 6166065; WO 9912900
📄 详细内容
合成路线:(R)-(+)-Limonene (I) is subjected to a free-radical sequential thiol-olefin cooxygenation in the presence of O2,thiophenol and di-tert-butyl peroxalate (DBPO) to furnish the sulfenyl endoperoxide (II) as a mixture of diastereoisomers.Chemoselective reduction of the hydroperoxide function of (II) with PPh3 yields alcohol (III).After oxidation of the sulfenyl group of (III) to the corresponding sulfone with mCPBA,the required isomer (IV) is isolated employing medium-pressure liquid chromatography.Finally,treatment of alcohol (IV) with phenyldiazomethane in the presence of trifluoromethanesulfonic acid gives rise to the O-benzylated derivative (1,2).
参考文献标题:A short synthesis and biological evaluation of potent and nontoxic antimalarial bridged bicyclic beta-sulfonyl-endoperoxides
文献作者:Bachi,M.D.; Korshin,E.E.; Hoos,R.; Szpilman,A.M.; Ploypradith,P.; Xie,S.; Shapiro,T.A.; Posner,G.H.
参考来源:J Med Chem 2003,46(12),2516