Losigamone, ADD-137022, AO-33-药物合成数据库

【药物名称】Losigamone, ADD-137022, AO-33

化学结构式(Chemical Structure):

参考文献No.	7337
标题:	5-Arylalkyl-4-alkoxy-2(5H)-furanone derivs., intermediates and process for their preparation as well as use as therapeutic agents
作者:	Chatterjee, S.S.; Klessing, K. (Willmar Schwabe GmbH)
来源:	DE 3615157; EP 0247320; JP 1988022087; US 4855320

合成路线图解说明: Condensation of 2-chlorobenzaldehyde (I) with methyl 3-methoxy-2(E)-butenoate (II) in the presence of a strong base in dimethyl sulfoxide/water affords, after acidification and reesterification by ethyl bromide/potassium carbonate ethyl 5-(2-chlorophenyl)-3-methyl-2(E),4(E)-pentadienoate (III). Osmium tetroxide catalyzed dihydroxylation of (III) in acetone/water with N-methylmorpholine-N-oxide (NMO) as cooxidant exclusively yields ethyl 5-(2-chlorophenyl)-4,5-threo-dihydroxy-3-methoxy-2(E)-pentenoate (IV), which in acidic medium spontaneously lactonizes to give the parent compound.

参考文献No.	147004
标题:	LOSIGAMONE < Prop INN >
作者:	N鰈dner, M.; Chatterjee, S.S.
来源:	Drugs Fut 1990,15(10),995

合成路线图解说明: Condensation of 2-chlorobenzaldehyde (I) with methyl 3-methoxy-2(E)-butenoate (II) in the presence of a strong base in dimethyl sulfoxide/water affords, after acidification and reesterification by ethyl bromide/potassium carbonate ethyl 5-(2-chlorophenyl)-3-methyl-2(E),4(E)-pentadienoate (III). Osmium tetroxide catalyzed dihydroxylation of (III) in acetone/water with N-methylmorpholine-N-oxide (NMO) as cooxidant exclusively yields ethyl 5-(2-chlorophenyl)-4,5-threo-dihydroxy-3-methoxy-2(E)-pentenoate (IV), which in acidic medium spontaneously lactonizes to give the parent compound.