422319-58-2

Upstream product

• 422319-57-1 C₃₅H₃₂Cl₃N₃O₇ 
• 422319-55-9 (2S,9R,9aS)-9-Hydroxy-2-isobutyl-9-[(R)-2-methoxycarbonyl-2-(2,2,2-trichloro-ethoxycarbonylamino)-ethyl]-3-oxo-2,3,9,9a-tetrahydro-imidazo[1,2-a]indole-1-carboxylic acid benzyl ester 
• 422319-56-0 C₂₀H₂₂Cl₃N₃O₅ 
• 316828-36-1 N_in-L-benzyloxycarbonylleucyl-N_a-2,2,2-trichloroethoxycarbonyl-2-iodo-D-tryptophan methyl ester 
• 316828-38-3 (2S,9R)-9-Hydroxy-2-isobutyl-9a-methoxy-9-[(R)-2-methoxycarbonyl-2-(2,2,2-trichloro-ethoxycarbonylamino)-ethyl]-3-oxo-2,3,9,9a-tetrahydro-imidazo[1,2-a]indole-1-carboxylic acid benzyl ester 
• 316828-34-9 methyl (αR,2S)-2,3-dihydro-2-(2-methylpropyl)-3-oxo-1-[(phenylmethoxy)carbonyl]-α-[[(2,2,2-trichloroethoxy)carbonyl]amino]-1H-imidazo(1,2-a)indole-9-propanoate 
• 316828-32-7 N_in-L-benzyloxycarbonylleucyl-N_a-2,2,2-trichloroethoxycarbonyl-D-tryptophan methyl ester 
• 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 
• 14907-27-8 (R)-(+)-tryptophan methyl ester hydrochloride 
• 2018-66-8 Z-Leu-OH 
• 118-92-3 anthranilic acid 

Downstream Products

• 422319-59-3 C₆₃H₅₅N₅O₉Se 

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.

Total Syntheses of (-)-Fumiquinazolines C, E, and H

matrix presented Total syntheses of the heptacyclic fumiquinazolines C and H have been accomplished efficiently using FmocNHCH(CH2SePh)CO2H as the precursor for the requisite dehydrofumiquinazoline.