85612-22-2

Upstream product

• 100-02-7 4-nitro-phenol 
• 91847-25-5 N-2,2,2-trichloroethoxycarbonyl-α-methylalanine 

Downstream Products

• 94141-33-0 (R)-2-[2-((S)-1-Acetoxy-2-methyl-propyl)-4-oxo-1,4-dihydro-2H-quinazolin-3-yl]-3-{1-[2-methyl-2-(2,2,2-trichloro-ethoxycarbonylamino)-propionyl]-1H-indol-3-yl}-propionic acid benzyl ester 
• 85612-24-4 benzyl 1-(N-(2,2,2-trichloroethoxy)carbonyl-α-methylalanyl)-3-indolepropionate 
• 85612-32-4 (S)-3-{1-[2-Methyl-2-(2,2,2-trichloro-ethoxycarbonylamino)-propionyl]-1H-indol-3-yl}-2-(4-oxo-4H-quinazolin-3-yl)-propionic acid benzyl ester 
• 94141-34-1 (R)-2-[2-((S)-1-Acetoxy-2-methyl-propyl)-4-oxo-4H-quinazolin-3-yl]-3-{1-[2-methyl-2-(2,2,2-trichloro-ethoxycarbonylamino)-propionyl]-1H-indol-3-yl}-propionic acid benzyl ester 

Relevant academic research and scientific papers

Synthesis of the Imidazoindole-spirolactone Ring System by Oxidative Double Cyclization. A Synthetic Approach to Tryptoquivalines

Imidazoindole-spirolactone 13, the principal ring system of tryptoquivalines, was succesfully synthesized by a new method via oxidative double cyclization of 1-(N-alkoxycarbonylalanyl)-3-indolepropionic acids (5) with N-bromosuccinimide, which were synthesized by acylation of benzyl 3-indolepropionate (10) with N-alkoxycarbonyl alanine p-nitrophenyl ester (12).The use of KF, 18-crown-6 and (iso-Pr)2NEt in acetonitrile lead to high yields of benzyl 1-(N-methoxycarbonyl-α-methylalanyl)-3-indolepropionates (4).The removal of the protecting group of 13c provided 2.The mechanisms of these reactions are discussed.Keywords - tryptoquivaline; imidazoindole-spirolactone; 1-(N-alkoxycarbonylalanyl)-3-indolepropionic acid; oxidative double cyclization; N-bromosuccinimide; acylation.