【药物名称】
化学结构式(Chemical Structure):
参考文献No.616012
标题:Atropisomeric derivatives of 2',6'-disubstituted (R)-11-phenylaporphine: Selective serotonin 5-HT7 receptor antagonist
作者:Linnanen, T.; Brisander, M.; Unelius, L.; Rosqvist, S.; Nordvall, G.; Hacksell, U.; Johansson, A.M.
来源:J Med Chem 2001,44(9),1337
合成路线图解说明:

Hydroxyaporphine (I) was converted to triflate (II) upon treatment with N-phenyl trifluoromethanesulfonimide (1). Suzuki coupling of triflate (II) with 2,6-dimethoxyphenylboronic acid (III) furnished the 11-aryl aporphine (IV). After cleavage of the methyl ether groups of (IV) with HBr, the resultant resorcinol derivative (V) was converted to the corresponding bis-triflate (VI) by means of N-phenyl trifluoromethanesulfonimide. Stereoselective introduction of a cyano group in (VI) was achieved by displacement of the less hindered triflate group with zinc cyanide in the presence of palladium catalyst, yielding the target (6aR,aR)-cyanide (VII) in 90% d.e. After isolation of the major isomer, the remaining triflate group of (VII) was displaced with tetramethylstannane to furnish the title compound.

参考文献No.803907
标题:
作者:
来源:J Med Chem 1996,393503-13
合成路线图解说明:

Hydroxyaporphine (I) was converted to triflate (II) upon treatment with N-phenyl trifluoromethanesulfonimide (1). Suzuki coupling of triflate (II) with 2,6-dimethoxyphenylboronic acid (III) furnished the 11-aryl aporphine (IV). After cleavage of the methyl ether groups of (IV) with HBr, the resultant resorcinol derivative (V) was converted to the corresponding bis-triflate (VI) by means of N-phenyl trifluoromethanesulfonimide. Stereoselective introduction of a cyano group in (VI) was achieved by displacement of the less hindered triflate group with zinc cyanide in the presence of palladium catalyst, yielding the target (6aR,aR)-cyanide (VII) in 90% d.e. After isolation of the major isomer, the remaining triflate group of (VII) was displaced with tetramethylstannane to furnish the title compound.

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