496961-80-9

Upstream product

• 1142-20-7 N-Cbz-Ala 
• 316828-44-1 methyl (αR,2S,9S)-2,3,9,9a-tetrahydro-9-hydroxy-9a-methoxy-2-methyl-3-oxo-1-[(phenylmethoxy)carbonyl]-α-[[(2,2,2-trichloroethoxy)carbonyl]amino]-1H-imidazo(1,2-a)indole-9-propanoate 
• 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 
• 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 
• 496961-79-6 C₂₆H₂₄Cl₃N₃O₈ 

Downstream Products

• 422319-32-2 C₅₃H₄₅N₅O₉Se 
• 422319-33-3 C₅₃H₄₃N₅O₈Se 
• 316828-50-9 C₄₇H₄₁N₅O₉ 
• 316828-49-6 C₄₇H₄₁N₅O₉ 
• 316828-52-1 C₄₇H₃₉N₅O₈ 
• 316828-51-0 C₄₇H₃₉N₅O₈ 
• 316828-57-6 14-epi-N-19-benzyloxycarbonyl-fumiquinazoline B 
• 316828-55-4 (2S,9S,9aR)-9-Hydroxy-2-methyl-9-((1S,4S)-1-methyl-3,10-dioxo-1,3,4,10-tetrahydro-2H-2,4a,9-triaza-anthracen-4-ylmethyl)-3-oxo-2,3,9,9a-tetrahydro-imidazo[1,2-a]indole-1-carboxylic acid benzyl ester 
• 316828-54-3 N-19-benzyloxycarbonyl-fumiquinazoline B 
• 316828-53-2 N-19-benzyloxycarbonyl-fumiquinazoline A 
• 316828-48-5 C₂₉H₂₆N₄O₆ 
• 140715-85-1 fumiquinazoline A 
• 316828-46-3 C₂₅H₂₂Cl₃N₃O₇ 

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.