878626-89-2

Upstream product

• 878626-79-0 (E)-(S)-4-tert-butoxycarbonylamino-2-methyl-5-(triphenylmethylthio)pentanoic acid ethyl ether 
• 157944-68-8 2-(diethoxyphosphoryl)propionic acid allyl ester 
• 197454-20-9 (S)-5,5-dimethyl-4-hydroxyhexan-2-one 
• 67760-86-5 (3S)-2,2-dimethyl-5-hexen-3-ol 
• 916912-38-4 (E)-(S)-4-(9H-Fluoren-9-ylmethoxycarbonylamino)-2-methyl-5-tritylsulfanyl-pent-2-enoic acid allyl ester 
• 887628-07-1 [1-(methoxy-methyl-carbamoyl)-2-tritylsulfanyl-ethyl]-carbamic acid 9H-fluoren-9-ylmethyl ester 
• 612492-46-3 (S)-Pyrrolidine-1,2-dicarboxylic acid 2-((1S,3S,5S,6S)-1-tert-butyl-6-carboxy-5-hydroxy-3-methyl-heptyl) ester 1-(9H-fluoren-9-ylmethyl) ester 
• 676324-76-8 (3S,5S)-5-(4-methoxybenzyloxy)-3,6,6-trimethylheptan-1-ol 
• 676324-77-9 (3R,5S)-5-(4-methoxybenzyloxy)-3,6,6-trimethylheptanal 
• 15761-39-4 1-(tert-butoxycarbonyl)-L-proline 
• 878626-80-3 (S)-Pyrrolidine-1,2-dicarboxylic acid 2-[(1S,3R,5S,6S)-6-((E)-(S)-3-allyloxycarbonyl-1-tritylsulfanylmethyl-but-2-enylcarbamoyl)-1-tert-butyl-5-(tert-butyl-dimethyl-silanyloxy)-3-methyl-heptyl] ester 1-tert-butyl ester 
• 878626-88-1 (S)-Pyrrolidine-1,2-dicarboxylic acid 2-[(1S,3S,5S,6S)-6-((E)-(S)-3-allyloxycarbonyl-1-tritylsulfanylmethyl-but-2-enylcarbamoyl)-1-tert-butyl-5-hydroxy-3-methyl-heptyl] ester 1-tert-butyl ester 
• 878626-78-9 (1R,3S,4S,6S,8S)-4-(tert-butyldimethylsilyloxy)-8-(4-methoxybenzyloxy)-1,3,6,9,9-pentamethyl-2-oxodecyl benzoate 
• 878626-74-5 (2E)-(4S)-4-N-tert-butoxycarbonylamino-2-methyl-5-(triphenylmethylthio)-2-pentenoic acid allyl ester 

Downstream Products

• 350791-64-9 (-)-apratoxin A 
• 878626-85-8 1-[(9H-fluoren-9-yl)methyl] 2-[(3S,5S,7S,8S)-8-({S}-4-{[5S,8S,11S,E]-11-[(S)-sec-butyl]-5-[4-methoxybenzyl]-2,7,8,10-tetramethyl-3,6,9,12-tetraoxo-13-oxa-4,7,10-triazahexadeca-1,15-dien-1-yl}-4,5-dihydrothiazol-2-yl)-7-hydroxy-2,2,5-trimethylnonan-3-yl] (S)-pyrrolidine-1,2-dicarboxylate 
• 878626-86-9 pyrrolidine-2-carboxylic acid 1-tert-butyl-6-(4-{2-[1-({1-[(1-carboxy-2-methyl-butyl)-methyl-carbamoyl]-ethyl}-methyl-carbamoyl)-2-(4-methoxy-phenyl)-ethylcarbamoyl]-propenyl}-4,5-dihydro-thiazol-2-yl)-5-hydroxy-3-methyl-heptyl ester 
• 878626-72-3 1-[(9H-fluoren-9-yl)methyl] 2-[(3S,5S,7S,8S)-9-{[(S,E)-5-(allyloxy)-4-methyl-5-oxo-1-(tritylthio)pent-3-en-2-yl]amino}-2,2,5,8-tetramethyl-9-oxo-7-{[(2,2,2-trichloroethoxy)carbonyl]oxy}nonan-3-yl] (S)-pyrrolidine-1,2-dicarboxylate 

Relevant academic research and scientific papers

Total synthesis of apratoxin A

We have achieved a total synthesis of apratoxin A in which thiazoline formation was accomplished from the moCys containing amide 4 using PPh 3(O)/Tf2O. Deprotection of the Troc and allyl ester in 17, coupling with tripeptide 3, and d

Total synthesis of the cyclodepsipeptide apratoxin A and its analogues and assessment of their biological activities

A novel total synthesis of apratoxin A is described, with key steps including the assembly of its ketide segment through a D-proline-catalyzed direct aldol reaction and Oppolzer's anti aldol reaction and the preparation of its thiazoline unit in a biomimetic synthesis. An oxazoline analogue of apratoxin A has also been elaborated by a similar approach. This compound has a potency against HeLa cell proliferation only slightly lower than that of apratoxin A, whilst a C(40)-demethylated oxazoline analogue of apratoxin A displays a much lower cytotoxicity and the C(37)-epimer and C(37) demethylation prod uct of this new analogue are inactive. These results suggest that the two methyl groups at C(37) and C(40) and the stereochemistry at C(37) are essential for the potent cellular activity of the oxazoline analogue of apratoxin A. Further biological analysis revealed that both synthetic apratoxin A and its oxazoline analogue inhibited cell proliferation by causing cell cycle arrest in the G1 phase.