110527-68-9

Upstream product

• 67-56-1 methanol 
• 2279-15-4 carbobenzyloxy-L-trytophan 
• 911675-22-4 (S)-2-(((benzyloxy)carbonyl)amino)-3-(2-oxoindolin-3-yl)propanoic acid 

Downstream Products

• 110527-66-7 methyl 2-benzyloxycarbonylamino-3-(2-thioxo-3-indolinyl)propanoate 
• 96838-39-0 (S)-2-benzyloxycarbonylamino-3-(2-methylthio-3-indolyl)propanoic acid 
• 96838-38-9 methyl (S)-2-benzyloxycarbonylamino-3-(2-methylthio-3-indolyl)propanoate 
• 96838-41-4 (R)-2-[(S)-2-Benzyloxycarbonylamino-3-(2-methylsulfanyl-1H-indol-3-yl)-propionylamino]-3-(2-methylsulfanyl-1H-indol-3-yl)-propionic acid methyl ester 

Relevant academic research and scientific papers

TOTAL SYNTHESIS OF AMAUROMINE

A total synthesis of amauromine (1) is described.Starting with L-tryptophan, diketopiperazine 4 was synthesized in nine steps.Thio-Claisen rearrangement of the sulphonium cation derived from the key intermediate 4 proceeded at the two sites simultaneously to provide 3 along with 12.Reductive desulphurization on 3 using TiCl4-LiAlH4 (1:2) resulted in concurrent cyclization to lead to amauromine (1).