1007893-75-5

Upstream product

• 1007893-74-4 (4-hydroxyphenyl)(9H-pyrido[3,4-b]indol-1-yl)methanone 
• 61-54-1 tryptamine 
• 768-60-5 4-methoxyphenylacetylen 
• 3610-42-2 5-bromotryptamine 
• 99-93-4 4-Hydroxyacetophenone 
• 131653-79-7 (E)-5-bromo-3-(2-nitroethenyl)-1H-indole 
• 10075-50-0 5-bromo-1H-indole 
• 100-06-1 1-(4-methoxyphenyl)ethanone 
• 1076-95-5 p-methoxyphenylglyoxal 
• 123475-33-2 2-(5'-Bromo-3'-indolyl)-1-nitroethane 
• 74447-37-3 4-methylsulphonyloxyphenylacetaldehyde 
• 74447-38-4 4-(2-hydroxyethyl)phenyl methanesulfonate 
• 1435263-75-4 4-(6-bromo-9H-pyrido[3,4-b]indole-1-carbonyl)phenyl methanesulfonate 
• 1435263-54-9 4-((6-bromo-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-1-yl)methyl)phenyl methanesulfonate 

Downstream Products

• 1007893-79-9 (6-bromo-9H-pyrido[3,4-b]indol-1-yl)(3,5-dibromo-4-hydroxyphenyl)methanone 

Relevant academic research and scientific papers

Iodine-mediated oxidative Pictet-Spengler reaction using terminal alkyne as the 2-oxoaldehyde surrogate for the synthesis of 1-aroyl-β-carbolines and fused-nitrogen heterocycles

An efficient iodine-mediated oxidative Pictet-Spengler reaction in dimethyl sulphoxide (DMSO) using terminal alkynes as the 2-oxoaldehyde surrogate for the synthesis of aryl (9H-pyrido[3,4-b]indol-1-yl)methanones is described. The scope of the protocol includes the total synthesis of Fascaplysin, Eudistomins Y1 and Y2. The methodology is extended for preparing pyrrolo[1,2-a]-quinoxaline and indolo[1,5-a]quinoxaline derivatives. The utility of 1-aroyl-β-carbolines was demonstrated by performing palladium-catalyzed β-carboline directed ortho-C(sp2)-H functionalization of the phenyl ring with thiomethyl (SMe) group using DMSO as source and for accessing 4-aryl-canthin-6-ones.

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

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.

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

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 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%.