HU-308-药物合成数据库

【药物名称】HU-308

化学结构式(Chemical Structure):

参考文献No.	559199
标题:	HU - 308: A specific agonist for CB2, a peripheral cannabinoid receptor
作者:	Hanus, L.; Breuer, A.; Tchilibon, S.; Shiloah, S.; Goldenberg, D.; Horowitz, M.; Pertwee, R.G.; Ross, R.A.; Mechoulam, R.; Fride, E.
来源:	Proc Natl Acad Sci USA 1999, 96(25): 14228 1999,96(25),14228

合成路线图解说明: Esterification of (1S,5R)-myrtenol (I) with pivalyl chloride (II) yields ester (III), which is then oxidized with Na2CrO4 in HOAc-Ac2O to give 4-oxo-myrtenyl pivalate (IV). Reduction of (IV) with lithium tri-t-butoxyaluminohydride in THF affords 4-hydroxymyrtenyl pivalate (V), which is then condensed with 5-(1,1-dimethylheptyl)resorcinol (VI) in the presence of p-TsOH in CH2Cl2 to furnish compound (VII). Treatment of (VII) with K2CO3 in MeOH provides methyl ether derivative (VIII), which is finally reduced with LiAlH4.

参考文献No.	603389
标题:	Synthesis of the individual, pharmacologically distinct, enantiomers of a tetrahydrocannabinol derivative
作者:	Mechoulam, R.; et al.
来源:	Tetrahedron Asymmetry 1990,1(5),315

合成路线图解说明: Esterification of (1S,5R)-myrtenol (I) with pivalyl chloride (II) yields ester (III), which is then oxidized with Na2CrO4 in HOAc-Ac2O to give 4-oxo-myrtenyl pivalate (IV). Reduction of (IV) with lithium tri-t-butoxyaluminohydride in THF affords 4-hydroxymyrtenyl pivalate (V), which is then condensed with 5-(1,1-dimethylheptyl)resorcinol (VI) in the presence of p-TsOH in CH2Cl2 to furnish compound (VII). Treatment of (VII) with K2CO3 in MeOH provides methyl ether derivative (VIII), which is finally reduced with LiAlH4.