676324-76-8

Upstream product

• 676324-75-7 (4S)-3-[(3R,5S)-5-(4-methoxybenzyloxy)-3,6,6-trimethylheptanoyl]-4-phenyloxazolidin-2-one 
• 197454-20-9 (S)-5,5-dimethyl-4-hydroxyhexan-2-one 
• 1046471-34-4 (R)-3-methylglutaric acid mono-n-propyl ester 
• 676324-74-6 (4S)-3-[(5S)-5-(4-methoxybenzyloxy)-6,6-dimethylhept-2-enoyl]-4-phenyloxazolidin-2-one 
• 676324-73-5 (3S)-3-(para-methoxybenzyloxy)-4,4-dimethylpentanal 
• 89238-99-3 O-(4-methoxybenzyl)-trichloroacetimidate 
• 878626-76-7 acetic acid 1-[2-(4-methoxy-benzyloxy)-3,3-dimethyl-butyl]-1-methyl-allyl ester 
• 878626-87-0 (S)-5,5-dimethyl-4-(4-methoxybenzyloxy)-2-hexanone 
• 878626-77-8 (E)-(S)-5-(4-methoxybenzyloxy)-3,6,6-trimethyl-2-hepten-1-ol 

Downstream Products

• 676324-81-5 (3R,4S,6S,8S)-8-(4-methoxybenzyloxy)-3,6,9,9-tetramethyl-4-(tert-butyldimethylsilanyloxy)dec-1-ene 
• 676324-80-4 (3R,4S,6S,8S)-8-(4-methoxybenzyloxy)-3,6,9,9-tetramethyldec-1-en-4-ol 
• 582321-75-3 pyrrolidine-1,2-dicarboxylic acid (2S)-2-[(1S,3S,5S,6S,8R)-8-benzoyloxy-1-tert-butyl-5-(tert-butyldimethylsilyloxy)-3,6-dimethyl-7-oxononyl] ester 1-tert-butyl ester 
• 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 
• 878626-72-3 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 
• 878626-89-2 (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-(9H-fluoren-9-ylmethyl) ester 
• 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 
• 878626-80-3 (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 
• 676324-77-9 (3R,5S)-5-(4-methoxybenzyloxy)-3,6,6-trimethylheptanal 

Relevant academic research and scientific papers

Synthesis of a biphenylalanine analogue of apratoxin a displaying substantially enhanced cytotoxicity

The concise synthesis of the 3,7-dihydroxy-2,5,8,8-tetramethylnonanoic acid moiety of apratoxin A and the total synthesis of compound 3, a 4-biphenylalanine (Bph) analogue of apratoxin A, have been demonstrated. The Bph analogue 3 exhibited a 16-fold increase in cytotoxicity against HCT-116 cells with respect to apratoxin A. This evidence indicated that existing the 4-phenyl group of Bph in 3 significantly enhanced its cytotoxicity, a conclusion corroborated by the 100-fold difference in cytotoxicity against HCT-116 cells observed between apratoxin M7 and apratoxin M16, which is characterized by the presence of a 4-phenyl group where apratoxin M7 displays a 4-methoxy group. Results from a conformational study using a distance geometry method suggested that 3 and apratoxin A adopt similar conformations in CD3CN.

Total synthesis of (-)-apratoxin A, 34-epimer, and its oxazoline analogue

A concise and convergent total synthesis of the highly cytotoxic marine natural product apratoxin A is accomplished by an 18-step linear sequence. The high sensitivity of the thiazoline, bearing an adjacent β-hydroxyl group at the C35-position, results in

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

Synthesis of the polyketide segment of apratoxin A

Apratoxin A 1 is a potent cytotoxic agent extracted from a marine cyanobacterium. We report the results of our synthetic approaches to the polyketide segment 3-OTBS-7-OPMB-2,5,8,8-tetramethylnonanoic acid 4, and the scope and limitations of these approach