496962-33-5

Upstream product

• 35661-39-3 N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine 
• 496961-70-7 (S)-9-[(R)-2-(2-Amino-benzoylamino)-2-methoxycarbonyl-ethyl]-2-methyl-3-oxo-2,3-dihydro-imidazo[1,2-a]indole-1-carboxylic acid benzyl ester 
• 496961-90-1 (S)-9-((R)-2-Amino-2-methoxycarbonyl-ethyl)-2-methyl-3-oxo-2,3-dihydro-imidazo[1,2-a]indole-1-carboxylic acid benzyl ester 
• 316828-35-0 N_in-L-benzyloxycarbonylalanyl-N_a-2,2,2-trichloroethoxycarbonyl-2-iodo-D-tryptophan methyl ester 
• 316828-33-8 methyl (αR,2S)-2,3-dihydro-2-methyl-3-oxo-1-[(phenylmethoxy)carbonyl]-α-[[(2,2,2-trichloroethoxy)carbonyl]amino]-1H-imidazo(1,2-a)indole-9-propanoate 
• 316828-31-6 N_in-L-benzyloxycarbonylalanyl-N_a-2,2,2-trichloroethoxycarbonyl-D-tryptophan methyl ester 
• 118-92-3 anthranilic acid 
• 14907-27-8 (R)-(+)-tryptophan methyl ester hydrochloride 
• 1142-20-7 N-Cbz-Ala 
• 316828-59-8 3-(2,3-dihydro-1H-indol-3-yl)-2-(2,2,2-trichloro-ethoxycarbonylamino)-propionic acid methyl ester 
• 316828-30-5 N_α-2,2,2-trichloroethoxycarbonyl-D-tryptophan methyl ester 

Downstream Products

• 496961-71-8 9-(2-{2-[1-(9H-fluoren-9-ylmethoxycarbonylamino)-ethyl]-benzo[d][1,3]oxazin-4-ylideneamino}-2-methoxycarbonyl-ethyl)-2-methyl-3-oxo-2,3-dihydro-imidazo[1,2-a]indole-1-carboxylic acid benzyl ester 

Relevant academic research and scientific papers

Total synthesis of (-)-fumiquinazolines A, B, C, E, H, and I. Approaches to the synthesis of fiscalin A

The first syntheses of (-)-fumiquinazolines A, B, and I, which proceed in 14 steps from protected tryptophan, anthranilic acid, leucine, and alanine in 7% overall yield, are described. Tricycle 30 was formed by a palladium-catalyzed cyclization. Oxidation of 30a with saccharine-derived oxaziridine 21 for fumiquinazolines A and B and oxidation of 30b with dimethyldioxirane for fumiquinazoline I selectively formed the appropriate imidazoindolone stereoisomers. Application of the Ganesan-Mazurkiewicz cyclization completed the syntheses. Efficient 14-step syntheses of (-)-fumiquinazolines C (7) and E (3) and a 15-step synthesis of (-)-fumiquinazoline H (8) using FmocNHCH(CH2SePh)CO2H as a dehydroalanine precursor that spontaneously eliminated benzeneselenol without oxidation under the cyclization conditions are also reported. Model 86 for fiscalins A with the H and OH anti to each other has been prepared, but the procedure that worked for the model failed with the fully functionalized side chain.