HU-308
Chemical Name: 1-[4(R)-[4-(1,1-Dimethylheptyl)-2,6-dimethoxyphenyl]-6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl]methanol
项目整合开发状态: Preclinical
项目研究机构: Hebrew University (Originator), University of Aberdeen (Originator)
合成路线: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.
📌 参考资料/链接：
参考文献标题:HU - 308: A specific agonist for CB2,a peripheral cannabinoid receptor
文献作者:Hanus,L.; Breuer,A.; Tchilibon,S.; Shiloah,S.; Goldenberg,D.; Horowitz,M.; Pertwee,R.G.; Ross,R.A.; Mechoulam,R.; Fride,E.
参考来源:Proc Natl Acad Sci USA 1999,96(25): 14228 1999,96(25),14228
📄 详细内容
合成路线: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.
参考文献标题:Synthesis of the individual,pharmacologically distinct,enantiomers of a tetrahydrocannabinol derivative
文献作者:Mechoulam,R.; et al.
参考来源:Tetrahedron Asymmetry 1990,1(5),315