142230-29-3

Downstream Products

• 142230-31-7 C₃₀H₂₈N₂O₃ 
• 142230-30-6 (-)-trans-methyl 2,9-dibenzyl-3-methoxycarbonyl-1,2,3,4-tetrahydro-9H-pyrido<3,4-b>indole-1-propionate 
• 119184-21-3 2,9-Dibenzyl-1-(2-methoxycarbonyl-ethyl)-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid methyl ester 
• 142230-31-7 C₃₀H₂₈N₂O₃ 

Relevant academic research and scientific papers

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.