157402-88-5

Upstream product

• 73-22-3 L-Tryptophan 
• 100-39-0 benzyl bromide 
• 111596-26-0 (1S,3S)-2-Benzyl-3-(cyanomethyl)-1-<(methoxycarbonyl)methyl>-1,2,3,4-tetrahydro-9H-pyrido<3,4-b>indole 
• 111619-15-9 (1S,3S)-2-Benzyl-3-(cyanomethyl)-1-<(methoxycarbonyl)methyl>-9-methyl-1,2,3,4-tetrahydro-9H-pyrido<3,4-b>indole 
• 66087-99-8 (3S)-3-amino-4-(1H-indol-3-yl)butanenitrile 
• 189828-36-2 (6S,8S,9S,10S)-12-Benzyl-9-cyano-8-hydroxy-5-methyl-6,7,8,9,10,11-hexahydro-6,10-epimino-5H-cyclooct[b]indole 
• 318269-57-7 C₂₃H₂₁N₃O 
• 157364-80-2 C₂₃H₂₁N₃O 
• 66087-98-7 (3S)-3-(Tosylamino)-4-(2-indolyl)butanenitrile 

Downstream Products

• 143120-74-5 (6S,10S,8E)-12-Benzyl-5-methyl-6,7,10,11-tetrahydro-6,10-epimino-5H-cyclooctindole-9-carbaldehyde 
• 122490-85-1 C₂₃H₂₄N₂O 

Relevant academic research and scientific papers

New asymmetric route to bridged indole alkaloids: Formal enantiospecific syntheses of (-)-suaveoline, (-)-raumacline and (-)-Nb-methylraumacline

The homologous nitrile 13 derived from L-tryptophan undergoes a modified Pictet-Spengler reaction with methyl propynoate, under conditions of kinetic control, to afford the cis-tetrahydro-β-carboline 15a (cis:trans = 77:23). After protection, Dieckmann-Thorpe cyclisation to the bridged keto nitrile 20 proceeds in 90% yield. Simple functional group modifications via the alcohol 21a and nitrile 22 (structures confirmed by X-ray crystallography) allow convergence with the tetracyclic α,β-unsaturated aldehyde 10, which is an advanced intermediate for the synthesis of a range of bridged indole alkaloids.

A new asymmetric route to bridged indole alkaloids: Formal syntheses of (-)-suaveoline, (-)-raumacline and (-)-Nb-methylraumacline

When the homologated nitrile 11 derived from L-tryptophan undergoes a modified Pictet-Spengler reaction with methyl propynoate, the resulting cis-tetrahydro-β-carboline 12a is ideally functionalised for cyclisation to the bridged ketonitrile 14; simple functional group modifications via the nitrile 15 (structure confirmed by X-ray crystallography) allow convergence with the tetracyclic α,β-unsaturated aldehyde 10, which is an advanced intermediate for the synthesis of a range of bridged indole alkaloids.

Use of the Kinetically Controlled Pictet-Spengler Reaction in the Asymmetric Synthesis of Indole Alkaloids: Formal Syntheses of (-)-Ajmaline, (-)-Koumine, (-)-Taberpsychine, (-)-Koumidine and (-)-Suavoline

By employing the kinetically controlled Pictet-Spengler reaction L-tryptophan was used as the chiral starting material for the synthesis of the cis-1,3-disubstituted tetrahydro-β-carboline 14a.Protection of the two nitrogens and subsequent cyclisation/dec