866398-21-2Relevant articles and documents
Enantioselective synthesis of (-)-CP-55940 via ruthenium-catalyzed asymmetric hydrogenation of ketones
Cheng, Li-Jie,Xie, Jian-Hua,Wang, Li-Xin,Zhou, Qi-Lin
, p. 1105 - 1113 (2012/05/21)
A new and efficient catalytic asymmetric synthesis of the potent cannabinoid receptor agonist (-)-CP-55940 has been developed by using ruthenium-catalyzed asymmetric hydrogenation of racemic α-aryl ketones via dynamic kinetic resolution (DKR) as a key step. With RuCl2-SDPs/ diamine [SDPs=7,7'-bis(diarylphophino)-1,1'-spirobiindane] catalysts the asymmetric hydrogenation of racemic α-arylcyclohexanones via DKR provided the corresponding cis-β-arylcyclohexanols in high yields with up to 99.3% ee and >99:1 cis-selectivities. Both ethylene ketal group at the cyclohexane ring and ortho-methoxy group at the phenyl ring of the substrates 6 have little effect on the selectivity and reactivity of the hydrogenations. Based on this highly efficient asymmetric ketone hydrogenation, (-)-CP-55940 was synthesized in 13 steps (the longest linear steps) in 14.6% overall yield starting from commercially available 3-methoxybenzaldehyde and 1,4-cyclohexenedione monoethylene acetal. Copyright
MODULATOR
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Page/Page column 15; 13, (2008/12/04)
The present invention relates to a compound of formula I, or a pharmaceutically acceptable salt thereof. Formula (I), wherein R1 and R2 are each independently H or alkyl; Y is an alkyl group. CONR3R4, COOR5SO2NR16R17, NHSO2R18 or CN; X is an aryl or heteroaryl group, each of which may be optionally substituted with one or more substituents selected from (CH2)mZ where Z is halogen, OH, CN, alkyl, alkoxy, NO2, CF3, CONR6R7, CN, NR8R9, COOR10 or NHCOR11 and m is 0 to 3; R3 to R11 are each independently H, alkyl or aryl, wherein said alkyl and aryl groups are optionally substituted by one or more substituents selected from halogen, OH, CN, alkyl, alkoxy, NO2, CF3, CONR12R13, CN, NH2, COOR14, NHCOR15, and CN; R12 to R18 are each independently H or alkyl, more preferably H or Me; n is 1 to 6; wherein the compound is other than 3′,5′-dimethyl-4-(1,1-dimethylheptyl)-1,1′-biphenyl-2-ol. Further aspects of the invention related to the use of such compounds in the preparation of a medicament for the treatment of a muscular disorder, a gastrointestinal disorder, or for controlling spasticity or tremors.
Expedient synthesis of potent cannabinoid receptor agonist (-)-CP55,940
Itagaki, Noriaki,Sugahara, Tsutomu,Iwabuchi, Yoshiharu
, p. 4181 - 4183 (2007/10/03)
(Chemical Equation Presented) A stereocontrolled synthesis of (-)-CP55,940, a potent cannabinoid receptor agonist, has been attained using a novel aldolization/retroaldolization interconversion strategy, in which a temporarily generated chiral aldol motif plays essential roles.