1312602-64-4

Upstream product

• 1312602-69-9 C₂₅H₂₅NO₃ 
• 1312602-70-2 C₂₇H₂₇NO₃S₂ 
• 1312602-72-4 C₂₅H₂₅NO₂ 
• 1312602-65-5 C₂₄H₃₃NO₃Si 
• 4407-36-7 (2E)-3-phenyl-2-propen-1-ol 
• 136981-81-2 (R)-(E)-1,3-diphenyl-prop-2-en-1-ol 
• 297179-04-5 (R)-3-acetoxy-1,3-diphenyl-1-propene 
• 137134-65-7 (-)-(S,E)-3,5-diphenylpent-4-enoic acid 
• 1448603-02-8 (4R,5R,6S)-5-bromo-4,6-diphenyltetrahydropyran-2-one 
• 1448603-01-7 (R)-N-methyl-3-phenyl-3-((2S,3S)-3-phenyloxiran-2-yl)propanamide 

Relevant academic research and scientific papers

Magnesium-coordinated chelation control in 1,3-dipolar cycloaddition of chiral α-alkoxymethyl ether nitrile oxide: Application to the synthesis of (-)/(-)- cis -clausenamide

A facile regio- and diastereoselective nitrile oxide cycloaddition method using magnesium-coordinated chelation control of chiral α-alkoxymethyl ether nitrile oxide is reported. This reaction could be successfully applied as a key step in both the formal total synthesis of (-)-clausenamide and the total synthesis of (-)-cis-clausenamide.

Novel concise synthesis of (-)-clausenamide

A six-step synthesis of (-)-clausenamide is described. Optically pure (R,E)-1,3-diphenylallylic alcohol was acetylated and then subjected to an Ireland-Claisen rearrangement, giving the γ,δ-unsaturated acid, which underwent a substrate-induced stereoselective bromolactonization to afford the expected all-equatorial substituted bromo-δ-lactone. An unusual chemo-selective aminolysis of the lactone resulted in the formation of a γ,δ-epoxy-amide in stereospecific manner. Base-promoted cyclization of this intermediate and the subsequent Davis oxidation furnished the synthesis, delivering the final product in >99% ee and up to 34% overall yield. Copyright

Selective 3- and 6-OH modification of (-)-clausenamide

(-)-Clausenamide is a drug candidate under Phase I clinical trial for treatment of Alzheimer's disease (AD). In order to elucidate the substituent related structure-activity relationship, six one-substituent modified (-)-clausenamide analogues were designed, and four of them, namely 3-O-methyl, 6-O-methyl, 3-des-hydroxyl and 6-des-hydroxyl analogues were prepared by selective 3- and 6-OH modification of (-)-clausenamide.