143120-74-5

Basic information

• Product Name: (6S,10S,8E)-12-Benzyl-5-methyl-6,7,10,11-tetrahydro-6,10-epimino-5H-cyclooctindole-9-carbaldehyde

Upstream product

• 318269-57-7 C₂₃H₂₁N₃O 
• 100-39-0 benzyl bromide 
• 73-22-3 L-Tryptophan 
• 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 
• 157364-80-2 C₂₃H₂₁N₃O 
• 66087-98-7 (3S)-3-(Tosylamino)-4-(2-indolyl)butanenitrile 
• 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 
• 84129-60-2 trans-(1S,3R)-(-)-2-benzyl-3-methoxycarbonyl-1-methoxycarbonylethyl-9-methyl-1,2,3,4-tetrahydro-9H-pyrido<3,4-b>indole 
• 188067-60-9 (R)-methyl 2-amino-3-(1-methyl-1H-indol-3-yl)propanoate 
• 19779-74-9 (R)-3-(1-Methyl-1H-indol-3-yl)-2-{[1-phenyl-meth-(E)-ylidene]-amino}-propionic acid methyl ester 
• 100-52-7 benzaldehyde 
• 157402-88-5 (6S,10S,8E)-12-Benzyl-9-cyano-5-methyl-6,7,10,11-tetrahydro-6,10-epimino-5H-cyclooct[b]indole 

Downstream Products

• 143065-06-9 (6S,8S,9S,10S,1'R)-5-methyl-8-(1'-ethyl-2'-pentenyl)-9-(1',3'-dioxolan-2'-yl)-12-benzyl-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooctindole 
• 143065-02-5 (-)-(6S,8S,9S,10S,1'S)-5-methyl-8-(1'-ethyl-2'-pentenyl)-9-(1',3'-dioxolan-2'-yl)-12-benzyl-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooctindole 
• 143065-05-8 (-)-N_b-benzylraumacline 
• 143120-76-7 (-)-(6S,10S)-5-methyl-8-(1'-ethyl-2'-pentenyl)-12-benzyl-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooctindole-9-carboxaldehyde 
• 143065-00-3 (-)-(6S,10S)-5-methyl-8-(1'-ethyl-2'-pentenyl)-12-benzyl-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooctindole-9-carboxaldehyde 
• 143167-04-8 (-)-(6S,10S)-5-methyl-8-(1'-ethyl-2'-pentenyl)-12-benzyl-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooctindole-9-carboxaldehyde 
• 143065-04-7 (-)-(6S,8S,9S,10S,1'S)-5-methyl-8-(1'-ethyl-2'-hydroxyethyl)-9-(1',3'-dioxolan-2'-yl)-12-benzyl-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooctindole 
• 141804-40-2 5-methyl-9-butyryloxymethyl-12-benzyl-6,7,10,11-tetrahydro-6,10-imino-5H-cyclooctindole 
• 318269-63-5 (6S,10S)-12-Benzyl-5-methyl-6,7,10,11-tetrahydro-5H-6,10-iminocycloocta[b]indole-9-carbaldehyde ethylene acetal 
• 143064-99-7 (-)-(6S,10S)-5-methyl-9-(2'-ethyl-1'-hydroxy-3'-hexenyl)-12-benzyl-6,7,10,11-tetrahydro-6,10-imino-5H-cyclooct[b]indole 
• 210552-30-0 C₃₀H₃₆N₂O 
• 122490-85-1 C₂₃H₂₄N₂O 
• 122490-85-1 5-methyl-9-hydroxymethyl-12-benzyl-6,7,10,11-tetrahydro-6,10-imino-5H-cyclooctindole 
• 210552-31-1 C₃₂H₄₀N₂O₂ 

Relevant articles and documents

General Approach to the Synthesis of Sarpagine and Ajmaline Alkaloids. Enantiospecific Total Synthesis of (+)-Ajmaline and Alkaloid G via the Asymmetric Pictet-Spengler Reaction

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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.

Enantiospecific total synthesis of the ajmaline related alkaloids (-)-suaveoline, (-)-raumacline, and (-)-N(b)-methylraumacline

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