137134-65-7

Upstream product

• 297179-04-5 (R)-3-acetoxy-1,3-diphenyl-1-propene 
• 136981-81-2 (R)-(E)-1,3-diphenyl-prop-2-en-1-ol 

Downstream Products

• 1312602-64-4 (4R,5R)-5-((S)-hydroxy(phenyl)methyl)-1-methyl-4-phenyl-pyrrolidin-2-one 
• 1448603-01-7 (R)-N-methyl-3-phenyl-3-((2S,3S)-3-phenyloxiran-2-yl)propanamide 
• 1448603-02-8 (4R,5R,6S)-5-bromo-4,6-diphenyltetrahydropyran-2-one 

Relevant academic research and scientific papers

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