104371-22-4

Upstream product

• 18917-77-6 (3,5-dimethoxyphenyl)acetone 
• 2627-86-3 (S)-1-phenyl-ethylamine 
• 1206475-87-7 (2S)-1-(3',5'-dimethoxyphenyl)-N-(tert-butoxycarbonyl)-2-aminopropane 

Downstream Products

• 1206475-90-2 (2S)-N-(2''-methyl-4''-methoxy-5''-methoxymethyl-6''-naphthyl)-1-(3',5'-dimethoxyphenyl)-2-aminopropane 
• 1206475-93-5 (2S)-N-(2''-methyl-4''-methoxy-5''-methoxymethyl-3''-naphthyl)-1-(3',5'-dimethoxyphenyl)-2-aminopropane 
• 1206475-95-7 (S)-N-(2''-methyl-4'',5''-dimethoxy-1''-naphthyl)-1-(3',5'-dimethoxyphenyl)-2-aminopropane 
• 1206475-86-6 2S-N-(2''-methyl-4'',5''-dimethoxy-8''naphthyl)-1-(3',5'-dimethoxyphenyl)-2-aminopropane 
• 104292-13-9 1-Bromo-4,5-dimethoxy-naphthalene-2-carboxylic acid (1S,3S)-2-benzyl-8-methoxy-1,3-dimethyl-1,2,3,4-tetrahydro-isoquinolin-6-yl ester 
• 104292-15-1 (1S,3S)-2-Benzyl-5-(2-hydroxymethyl-4,5-dimethoxy-naphthalen-1-yl)-8-methoxy-1,3-dimethyl-1,2,3,4-tetrahydro-isoquinolin-6-ol 
• 104292-16-2 (1S,3S)-2-Benzyl-5-(4,5-dimethoxy-2-methyl-naphthalen-1-yl)-8-methoxy-1,3-dimethyl-1,2,3,4-tetrahydro-isoquinolin-6-ol 
• 104292-14-0 (12S,14S)-13-Benzyl-1,6,7-trimethoxy-12,14-dimethyl-11,12,13,14-tetrahydro-3-oxa-13-aza-dibenzo[c,g]phenanthren-4-one 
• 104292-12-8 (1S,3S)-2-Benzyl-8-methoxy-1,3-dimethyl-1,2,3,4-tetrahydro-isoquinolin-6-ol 
• 32221-59-3 ancistrocladine 

Relevant academic research and scientific papers

Total synthesis of the N,C-coupled naphthylisoquinoline alkaloids ancistrocladinium A and B and related analogues

The N,C-coupled naphthyldihydroisoquinoline alkaloids ancistrocladinium A (3) and B (4), which possess an unprecedented iminium-aryl axis and show high in vitro antileishmanial activities, have been synthesized via a short sequence of eight linear steps, without the need of protecting groups. Key steps were a Buchwald-Hartwig amination and a Bischler-Napieralski cyclization, preferentially leading to the naturally predominant M-atropo-diastereomer in the case of 3, while the N,C-axis is configurationally semistable in 4. The highly convergent first access to this type of alkaloids will now facilitate the preparation of structural analogues for structure-activity relationship studies. Its general applicability was shown by the preparation of the sterically even more congested, as yet unnatural N,3′- and N,1′-coupled analogues, ancistrocladinium C (5) and D (6).