【药物名称】
化学结构式(Chemical Structure):
参考文献No.46374
标题:2,3-Dioxabicyclo[3.3.1]nonane derivs. and antimalarial pharmaceutical compsns. comprising them
作者:Posner, G.H.; Bachi, M.; Korshin, E. (Johns Hopkins University; Yeda Research & Development Co. Ltd.)
来源:US 6166065; WO 9912900
合成路线图解说明:

(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No.735381
标题:A short synthesis and biological evaluation of potent and nontoxic antimalarial bridged bicyclic beta-sulfonyl-endoperoxides
作者:Bachi, M.D.; Korshin, E.E.; Hoos, R.; Szpilman, A.M.; Ploypradith, P.; Xie, S.; Shapiro, T.A.; Posner, G.H.
来源:J Med Chem 2003,46(12),2516
合成路线图解说明:

(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).

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