157397-42-7

Upstream product

• 61-54-1 tryptamine 
• 72155-45-4 Boc-L-phenylalaninal 

Downstream Products

• 157397-44-9 methyl (1R,1'S)-1-<1'-(tert-butoxycarbonylamino)-2'-phenylethyl>-1,2,3,4-tetrahydro-β-carboline-2-carboxylate 
• 157397-50-7 (+/-)-1-<1'-(tert-butoxycarbonylamino)-2'-phenylethyl>-β-carboline 
• 108335-05-3 eudistomin T 
• 157397-51-8 (+/-)-1-(1'-amino-2'-phenylethyl)-β-carboline 
• 157397-46-1 methyl (1R,1'S)-1-(1'-amino-2'-phenylethyl)-1,2,3,4-tetrahydro-β-carboline-2-carboxylate 

Relevant academic research and scientific papers

Diastereoselective Pictet-Spengler Reactions of L-(Boc)Phenylalaninal and L-(Boc)Prolinal: Biomimetic Syntheses of Eudistomin T and (-)-Woodinine

The diastereoselective Pictet-Spengler reaction of L-(Boc)phenylalaninal with tryptamine and the elaboration of this intermediate to the antibacterial compound eudistomin T and analogues of the antileukaemic compound eudistomidin B are described.We also report an efficient synthesis of the naturally occuring alkaloid (-)-woodinine from L-(Boc)prolinal and 5-bromotryptamine in three steps, using a diastereoselective Pictet-Spengler reaction.This approach affords, in addition, formal synthesis of the marine alkaloids eudistomins H and I.