1007893-77-7

Upstream product

• 143399-01-3 (3-bromo-4-methoxy-phenyl)-acetyl chloride 
• 3610-42-2 5-bromotryptamine 
• 95-56-7 2-hydroxybromobenzene 
• 10075-50-0 5-bromo-1H-indole 
• 1836-06-2 3-bromo-4-hydroxyacetophenone 
• 131653-79-7 (E)-5-bromo-3-(2-nitroethenyl)-1H-indole 
• 104-01-8 4-Methoxyphenylacetic acid 
• 774-81-2 (3-bromo-4-methoxy-phenyl)-acetic acid 
• 1435263-48-1 2-bromo-4-(2-oxoethyl)phenyl methanesulfonate 
• 1435263-42-5 2-(3-bromo-4-hydroxyphenyl)acetaldehyde 
• 196081-78-4 3-bromo-4-hydroxyphenylethyl alcohol 
• 1435263-84-5 2-bromo-4-(6-bromo-9H-pyrido[3,4-b]indole-1-carbonyl)phenyl methanesulfonate 
• 1435263-64-1 2-bromo-4-((6-bromo-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-1-yl)methyl)phenyl methanesulfonate 
• 1201916-23-5 C₁₈H₁₄Br₂N₂O 

Downstream Products

• 1384431-90-6 eudistomin Y₁₃ 
• 1384431-89-3 eudistomin Y₁₂ 
• 1384431-86-0 eudistomin Y₉ 

Relevant academic research and scientific papers

Total synthesis and biological activity of marine alkaloid eudistomins Y1-Y7 and their analogues

Eudistomin Y class compounds are a series of β-carbolines which was originally isolated from a marine turnicate or ascidian near the South Korea Sea. These compounds contain bromo-substituted groups, which is one of the typical characters of marine natural products. We report herein the chemical synthesis and biological evaluation of seven new β-carboline-based metabolites, Eudistomins Y1-Y7, and their hydroxyl-methylated phenyl derivatives. Using bromo-substituted tryptamines and bromo-substituted phenylglyoxals as the key intermediates, Eudistomins Y 1-Y7 and their derivatives were synthesized via the acid-catalyzed Pictet-Spengler reaction and fully characterized by 1H- and 13C-NMR and mass spectroscopy. Biological studies revealed that all of the compounds showed moderate growth inhibitory activity against breast carcinoma cell line MDA-231 with IC50 of 15-63 μM and the inhibitory activities of hydroxyl-methylated phenyl products were higher than that of the corresponding natural products Eudistomins Y 1-Y7.

A cascade coupling strategy for one-pot total synthesis of β-carboline and isoquinoline-containing natural products and derivatives

Multi-birds with one stone: A cascade coupling strategy was developed for the synthesis of β-carbolines. The method can direct the synthesis of β-carboline and isoquinoline-containing natural products with high yields. Moreover, this protocol can also be further applied towards the total synthesis of natural products fascaplysin and papaverin (see scheme). Copyright

Tandem iodine-mediated oxidations of tetrahydro-β-carbolines: Total synthesis of eudistomins Y1-Y7

An efficient iodine-mediated oxidation of tetrahydro-β-carbolines is described to yield aromatic β-carboline products with tandem C-H oxidation. The utility of the method was demonstrated in total syntheses of the alkaloids eudistomins Y1-Y7. The Royal Society of Chemistry.

Total syntheses of eudistomins Y1-Y7 by an efficient one-pot process of tandem benzylic oxidation and aromatization of 1-benzyl-3,4-dihydro-β-carbolines

The first total synthesis of eudistomin Y7 (7) and total syntheses of eudistomins Y1-Y6 (1-6) are described. An efficient room-temperature conversion of 1-benzyl-3,4-dihydro-β-carbolines (11) into 1-benzoyl-β-carbolines (14) by a one-pot process of tandem benzylic oxidation and aromatization as the key step of these total syntheses was also studied in detail. The first total synthesis of eudistomin Y 7 (7) and total syntheses of eudistomins Y1-Y6 (1-6) are described. An efficient room-temperature conversion of 1-benzyl-3,4-dihydro-β-carbolines (11) into 1-benzoyl-β-carbolines (14) by a one-pot process of tandem benzylic oxidation and aromatization as the key step of these total syntheses was also studied in detail. Copyright

Total synthesis of Eudistomins Y1-Y6

The first total synthesis of Eudistomins Y1-Y6, brominated phenolic β-carboline marine metabolites with a unique benzoyl moiety at C1, have been prepared in three steps, utilizing MAOS, in overall yields ranging from 6% to 25%.