302356-98-5

Upstream product

• 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 
• 60702-96-7 2-benzyl-3-(methoxycarbonyl)-9-methyl-1,2,3,4-tetrahydro-9H-pyrido<3,4-b>indole-1-propionic acid 
• 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 
• 153-94-6 D-tryptophan 
• 120056-44-2 cis-(1R,3R)-(+)-2-benzyl-3-methoxycarbonyl-1-methoxycarbonylethyl-9-methyl-1,2,3,4-tetrahydro-9H-pyrido<3,4-b>indole 
• 120053-66-9 D-(+)-N_a-methyl-N_b-benzyltryptophan methyl ester 
• 123719-38-0 D-(-)-N_a-methyltryptophan methyl ester hydrochloride 
• 110117-83-4 D-(+)-N_a-methyltryptophan 
• 4299-70-1 L-tryptophan methyl ester 
• 148022-32-6 (1R,3S)-2-Benzyl-1-(2-methoxycarbonyl-ethyl)-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid methyl ester 
• 142292-54-4 (1R,3S)-2-Benzyl-1-(2-methoxycarbonyl-ethyl)-9-methyl-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid methyl ester 
• 2738-25-2 (6S,10S)-(-)-methyl-5-methyl-9-oxo-12-benzyl-6,7,8,9,10,11-hexahydro-6,10-imino-5H-cyclooctindole-8-carboxylate 
• 19779-75-0 N_b-benzylidene-L-tryptophan methyl ester 

Relevant academic research and scientific papers

Enantiospecific total synthesis of the enantiomer of the indole alkaloid affinisine

The enantiomer of affinisine has been synthesized (from L-tryptophan) with 100% diastereoselectivity via the asymmetric Pictet-Spengler reaction coupled with a Pd°(enolate mediated) coupling process. This enantiomer has also been converted into a key inte

STEREOSPECIFICITY IN THE PICTET-SPENGLER REACTION. ENANTIOSPECIFIC SYNTHESIS OF (6S,10S)-(-)-5-METHYL-9-OXO-12-BENZYL-6,7,8,9,10,11-HEXAHYDRO-6,10-IMINO-5H-CYCLOOCTINDOLE, A TEMPLATE FOR PREPARATION OF MACROLINE/SARPAGINE ALKALOIDS

The synthesis of the tetracyclic ketone was carried out in enantiospecific fashion (>98percent ee) via the 1,3-transfer of chirality from Na-methyl, Nb-benzyl tryptophan methyl ester to the trans diastereomer in the Pictet-Spengler reaction.Although the condensation of 14 with aldehyde (15) in refluxing benzene generated the tetrahydro β-carbolines (4b/5b) in a kinetic ratio (72:28), epimerization (C-1) of the cis diastereomer into the trans isomer occurred stereospecifically under acidic conditions.Dieckmann cyclizatin of either the Na-methyl, Nb-benzyl-cis-(+)-5b or trans-(-)-4b diastereomer provided the cis-bicyclo-azanonane system at approximately the same rate, although the β-keto esters were antipodal, in contrast to results reported in the Na-benzyl series by Magnus.

PICTET-SPENGLER REACTIONS IN APROTIC MEDIA. Nb-BENZYL PROMOTED RETENTION OF OPTICAL ACTIVITY IN THE SYNTHESIS OF AN INDOLO SUBSTITUTED AZABICYCLONONANE, A KEY TEMPLATE FOR THE SYNTHESIS OF MACROLINE ALKALOIDS.

The Nb-benzyl group (see 7) has been employed in the Pictet-Spengler reaction in refluxing benzene to provide complete retention of optical activity in this process.The tetrahydro-β-carbolines 3b (trans) and 4b (cis) were independently converte