74904-71-5

Upstream product

• 1699-51-0 laudanosine 
• 90601-56-2 2-(β-N-2,2,2-Trichloroethoxycarbonyl-N-methyl-aminoethyl)-4,5,3',4'-tetramethoxystilbene 
• 74904-68-0 (E)-N-2-<2-<2-(3,4-dimethoxyphenyl)ethenyl>-4,5-dimethoxyphenyl>ethyl-N-methylhydroxylamine 
• 74904-62-4 cis-(+/-)laudanosine N-oxide 
• 1449213-94-8 (E)-N-(2-(3,4-dimethoxystyryl)-4,5-dimethoxyphenyl)formamide 
• 1449213-93-7 (E)-2-(2-(3,4-dimethoxystyryl)-4,5-dimethoxyphenyl)ethanamine 
• 1449213-92-6 (E)-4-(4,5-dimethoxy-2-((E)-2-nitrovinyl)styryl)-1,2-dimethoxybenzene 
• 1449213-91-5 (E)-2-(3,4-dimethoxystyryl)-4,5-dimethoxybenzaldehyde 
• 6380-23-0 3,4-dimethoxystyrene 
• 5392-10-9 2-bromo-4,5-dimethoxybenzaldehyde 

Downstream Products

• 2688-77-9 (S)-laudanosine 
• 85-63-2 (R)-laudanosine 
• 124616-15-5 2-(β-N-Ethoxycarbonyl-N-methyl-aminoethyl)-4,5,3',4'-tetramethoxystilbene 

Relevant academic research and scientific papers

Asymmetric total synthesis of (?)-javaberine A and (?)-epi-javaberine A based on catalytic intramolecular hydroamination of N-methyl-2-(2-styrylaryl)ethylamine

Asymmetric total synthesis of (?)-javaberine A and its epimer was achieved by utilizing two methods for isoquinoline synthesis, asymmetric hydroamination of N-methyl-2-(2-styrylaryl)ethylamine and Bischler-Napieralski cyclization. Intramolecular asymmetric hydroamination of N-methyl aminoalkene 4 was catalyzed by lithium amide–chiral bisoxazoline to give tetrahydroisoquinoline (S)-laudanosine with good enantioselectivity in excellent yield. N-Demethylation of (S)-laudanosine was accomplished by Polonovski-type reaction to give (S)-norlaudanosine. Condensation of (S)-norlaudanosine with homoveratric acid, and subsequent Bischler-Napieralski cyclization, LiAlH4 reduction, and O-demethylation furnished (8R,14S)-(?)-javaberine A, corresponding to antipode of natural javaberine A. (8S,14S)-(?)-Javaberine A, which corresponds to C14-epimer of natural javaberine A, was also successfully synthesized.

Catalytic asymmetric synthesis of (S)-laudanosine by hydroamination

Lithium amide-chiral bisoxazoline-catalyzed asymmetric intramolecular hydroamination was examined with respect to the structural variants of starting aminoalkenes. Substituents on the nitrogen and olefin of aminoalkenes were found to be important factors affecting reaction efficiency as well as enentioselectivity in the production of chiral tetrahydroisoquinolines and isoindolines. The catalytic asymmetric total synthesis of (S)-laudanosine highlights the utility of the asymmetric hydroamination.

The Characterization and Thermolysis of cis- and trans-(+/-)-Laudanosine N-Oxide

The isolation and characterization of cis- and trans-(+/-)-laudanosine N-oxide is described.Thermolysis of cis-(+/-)-laudanosine N-oxide afforded the new fused and bridged heterocyclic derivatives (3RS,3aRS,8aSR)-3-(3,4-dimethoxyphenyl)-5,6-dimethyoxy-1-methyl-3,3a,8,8a-tetrahydro-1H-indeno-isoxazole (18) and (1RS,2RS,4RS)-2-(3,4-dimethoxyphenyl)-8,9-dimethoxy-5,6-dihydro-2H-1,4-methano-4H-3,4-benzoxazocine (19); other products included (+/-)-laudanosine, the Cope elimination product, (E)-N-2--4,5-dimethoxyphenyl>ethyl-N-methylhydroxyalamine (4) and 1-(3,4-dimethoxybenzyl)-7,8-dimethoxy-3-methyl -1,3,4,5-tetrahydro-2,3-benzoxazepine (17), the product of a Meisenheimer rearrangement.By contrast, trans-(+/-)-laudanosine N-oxide gave (4) in nearly quantitative yield.Some of the possible mechanistic implications of these results are discussed