88704-45-4

Usage

InChI:InChI=1/C15H13N3/c1-2-5-12-10(4-1)11-7-9-17-15(14(11)18-12)13-6-3-8-16-13/h1-2,4-5,7,9,18H,3,6,8H2

Upstream product

• 126893-05-8 2-(4,9-Dihydro-3H-β-carbolin-1-yl)-pyrrolidine-1-carboxylic acid benzyl ester 
• 126893-04-7 N_b-(N-Z-prolyl)tryptamine 
• 125305-05-7 1-[4-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-butyryl]-3,4-dihydro-β-carboline-9-carboxylic acid methyl ester 
• 59378-82-4 N-(tert-butoxycarbonyl)pyrrolidine-2-carboxaldehyde 
• 73-22-3 L-Tryptophan 
• 69610-41-9 Boc-L-Pro-H 
• 7524-52-9 (S)-tryptophan methyl ester hydrochloride 
• 128638-08-4 2-[4-(4,9-Dihydro-3H-β-carbolin-1-yl)-4-oxo-butyl]-isoindole-1,3-dione 
• 61-54-1 tryptamine 
• 100571-67-3 2-<3-(1-carbomethoxyindolyl)>ethyl isocyanide 
• 1148-11-4 N-Benzyloxycarbonyl-L-proline 
• 38940-60-2 9H-pyrido[3,4-b]indole-1-carboxamide 
• 102991-38-8 1,2,3,4-tetrahydro-β-carboline-1-carboxylic acid 
• 108061-48-9 methyl 1,2,3,4-tetrahydro-β-carboline-1-carboxylate hydrochloride 

Downstream Products

• 88704-44-3 eudistomin H 

Relevant academic research and scientific papers

An efficient one-pot decarboxylative aromatization of tetrahydro-β-carbolines by using N-chlorosuccinimide: total synthesis of norharmane, harmane and eudistomins

A facile method for the synthesis of a variety of β-carbolines and their natural products such as norharmane (2a), harmane (2b), eudistomins I, N, T, and U (6, 7, 9 and 10, respectively) has been successfully developed via a decorboxylative aromatization tool by employing N-chlorosuccinimide (NCS) as a mild and efficient reagent. Gratifyingly, this reagent system proceeds in a one-pot manner and converted all the tetrahydro-β-carboline acids into their corresponding decorboxylative aromatic products with good to excellent yields. Additionally, this system works well in the case of tetrahydro-β-carboline esters to produce their aromatic partners in high yields.

PhI(OAc)2-mediated one-pot oxidative decarboxylation and aromatization of tetrahydro-β-carbolines: Synthesis of norharmane, harmane, eudistomin U and eudistomin i

Iodobenzene diacetate was employed as a mild and efficient reagent for one-pot oxidative decarboxylation of tetrahydro-β-carboline acids and dehydrogenation of tetrahydro-β-carbolines to access the corresponding aromatic β-carbolines. To the best of our knowledge this is the first synthesis of β-carbolines via a one-pot oxidative decarboxylation at ambient temperature. The utility of this protocol has been demonstrated in the synthesis of β-carboline alkaloids norharmane (2o), harmane (2p), eudistomin U (9) and eudistomin I (12).

The Chemistry of Vicinal Tricarbonyl Compounds. Short Synthesis of Eudistomins T, I and M

The formation of three novel 1,2,3-tricarbonyl compounds and their use in the total synthesis of eudistomins T, I and M is described.

1-(1-Pyrrolin-2-yl)-β-carbolines. Synthesis of Eudistomins H, I, and P

Three marine β-ccarboline alkaloids, eudistomin H, I, and P (5, 4, and 6), were synthesized.The Bischler-Napieralski reaction of N-(N-benzyloxycarbonylprolyl)tryptamine (11) gave the 3,4-dihydro-β-carboline (12), which was converted to eudistomin I (5) vi