321351-49-9

Upstream product

• 2859-78-1 4-Bromoveratrole 
• 321351-46-6 (3R)-7-chloro-3-(3,4-dimethoxyphenyl)-6-methylhept-6-en-1-ol 
• 321351-45-5 (6E)-(3R)-7-chloro-3-(3,4-dimethoxyphenyl)-6-methylhept-6-enoic acid 
• 321351-47-7 (5R)-1-chloro-5-(3,4-dimethoxyphenyl)-2-methyl-7-(phenylmethoxy)hept-1-en-1-ol 
• 321351-40-0 (6E)-(3(3R),4S)-3-[7-chloro-3-(3,4-dimethoxyphenyl)-6-methylhept-6-enoyl]-4-phenyloxazolidin-2-one 
• 321351-48-8 (3R)-3-(3,4-dimethoxyphenyl)-1-methyl-3-[(2-phenylmethoxy)ethyl]cyclopentene 

Downstream Products

• 321351-50-2 (4R)-4-(3,4-dimethoxyphenyl)-4-[(2-phenylmethoxy)ethyl]cyclohex-2-enole 
• 468-53-1 (-)-mesembrine 
• 321351-51-3 (4R)-4-(3,4-dimethoxyphenyl)-4-(2-hydroxyethyl)cyclohex-2-enole 
• 321351-52-4 (4R)-4-(3,4-dimethoxyphenyl)-4-(2-methanesulfonyloxyethyl)cyclohex-2-enole 

Relevant academic research and scientific papers

Enantioselective construction of cyclic quaternary centers: (-)-mesembrine

The preparation of the crystalline amide 2 is reported. Conjugate addition to 2 proceeded with the expected high diastereocontrol to give 3. This set the stage for subsequent intramolecular alkylidene C-H insertion to give, after ozonolysis and aldol condensation, (-)-mesembrine 1. Amide 2 should be a useful chiron for the enantioselective construction of cyclic quaternary centers.