959859-89-3

Upstream product

• 61-54-1 tryptamine 
• 24165-03-5 tritylsulfenyl chloride 

Downstream Products

• 959859-84-8 1-(2-phenylethyl)-1,2,3,4-tetrahydro-β-carboline 
• 181492-01-3 (R)-1-benzyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole 
• 99545-51-4 (S)-1-benzyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole 
• 959859-85-9 1-(4-nitrophenyl)-1,2,3,4-tetrahydro-β-carboline 
• 142696-56-8 (S)-1-phenyl-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole 
• 148261-76-1 (R)-1-phenyl-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole 
• 959859-87-1 1-pentyl-N-tritylsulfenyltetrahydro-β-carboline 

Relevant academic research and scientific papers

Asymmetric Synthesis of (R)-1-Alkyl-Substituted Tetrahydro-?-carbolines Catalyzed by Strictosidine Synthases

Stereoselective methods for the synthesis of tetrahydro-?-carbolines are of significant interest due to the broad spectrum of biological activity of the target molecules. In the plant kingdom, strictosidine synthases catalyze the C?C coupling through a Pictet–Spengler reaction of tryptamine and secologanin to exclusively form the (S)-configured tetrahydro-?-carboline (S)-strictosidine. Investigating the biocatalytic Pictet–Spengler reaction of tryptamine with small-molecular-weight aliphatic aldehydes revealed that the strictosidine synthases give unexpectedly access to the (R)-configured product. Developing an efficient expression method for the enzyme allowed the preparative transformation of various aldehydes, giving the products with up to >98 % ee. With this tool in hand, a chemoenzymatic two-step synthesis of (R)-harmicine was achieved, giving (R)-harmicine in 67 % overall yield in optically pure form.

Catalytic asymmetric Pictet-Spengler reactions via sulfenyliminium ions

(Chemical Equation Presented) From cations to chiral products: β-Carbo-lines can be synthesized with good enantioselectivity by the title reaction catalyzed by a chiral binol-derived Bronsted acid (see scheme, BHT = 3,5-di(tert-butyl)-4-hydroxytoluene). T