72690-85-8

Upstream product

• 90150-59-7 dimethyl 1-carbethoxy-3,4,5,6-tetrahydro-6-(2-methyl-1-propenyl)azepino<5,4,3-cd>indole-4,4-dicarboxylate 
• 388116-27-6 indole-4-boronic acid pinacol ester 
• 29702-35-0 (S)-2-amino-3-(4-(3-methylbut-2-en-1-yl)-1H-indol-3-yl)propanoic acid 
• 112435-20-8 6-(2-Methyl-propenyl)-1,3,5,6-tetrahydro-azepino[5,4,3-cd]indole-4,4-dicarboxylic acid diethyl ester 
• 65600-90-0 (4R,6S)-6-(2-Methyl-propenyl)-3,4,5,6-tetrahydro-1H-azepino[5,4,3-cd]indole-4-carboxylic acid methyl ester 
• 96562-73-1 4-(3-hydroxy-3-methyl-1-buten-1-yl)indole-3-carboxaldehyde 
• 79133-60-1 (E)-1-(3-dimethylaminomethylindol-4-yl)-3-methyl-1-buten-3-ol 
• 156482-15-4 3-[4-((E)-3-Hydroxy-3-methyl-but-1-enyl)-1H-indol-3-yl]-2-nitro-propionic acid methyl ester 
• 84935-70-6 dimethyl 1-carbethoxy-3,4-dihydro-6-(2-methyl-1-propenyl)azepino<5,4,3-cd>indole-4,4-dicarboxylate 
• 84935-69-3 dimethyl 1-carbethoxy-3,4-dihydro-6-(2-methylpropyl)-azepino<5,4,3-cd>indole-4,4-dicarboxylate 
• 84935-71-7 dimethyl 1-carbethoxy-3,4-dihydro-6-(1-bromo-2-methylpropyl)azepino<5,4,3-cd>indole-4,4-dicarboxylate 
• 112435-26-4 2-Formylamino-2-[4-(3-methyl-but-2-enoyl)-1H-indol-3-ylmethyl]-malonic acid diethyl ester 
• 65600-90-0 cis-methyl 1-(2-methylprop-1-enyl)-2,3,4,6-tetrahydro-1H-azepino[5,4,3-cd]indole-3-carboxylate 
• 1353674-06-2 methyl 2-(diphenylmethyleneamino)-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indol-3-yl)propanoate 

Relevant academic research and scientific papers

Syntheses without protection: A three-step synthesis of optically active clavicipitic acid by utilizing biomimetic synthesis of 4-bromotryptophan

The optically active clavicipitic acid (4), an ergot alkaloid, was synthesized by a three-step sequence from 4-bromoindole (1). The reaction of 1 with dl-serine (2) in the presence of Ac2O followed by enzymatic kinetic resolution gave (S)-4-bromotryptophan (3). The Heck reaction of 3 with 1,1-dimethylallylalcohol in aqueous media gave clavicipitic acid in one-pot.

Total Synthesis of (-)-Clavicipitic Acid via γ,γ-Dimethylallyltryptophan (DMAT) and Chemoselective C-H Hydroxylation

The first total synthesis of natural (-)-clavicipitic acid from ?,?-dimethylallyltryptophan (DMAT), its biosynthetic precursor, is described. This is done by regio- and chemoselective, remote, nondirected C(sp3)-H hydroxylation followed by amin

Synthesis of (±)- cis -clavicipitic acid by a Rh(I)-catalyzed intramolecular imine reaction

A new and short synthesis of racemic cis-clavicipitic acid was achieved by taking advantage of the double nucleophilic character of indole-4-pinacolboronic ester. Key to the success of the synthesis were an efficient and selective C-3 indole Friedel-Craft

Enantioselective synthesis of (-)-cis-clavicipitic acid

(Chemical Equation Presented) An enantioselective synthetic method for (-)-cis-clavicipitic acid (1) was reported. 1 was obtained in 10 steps (99% ee and 20% overall yield) from 1H-indole-3-carboxylic acid methyl ester (9) via asymmetric phase-transfer ca

SYNTHESES OF (+/-)-CLAVICIPITIC ACID AND ITS DERIVATIVES

A formal total synthesis of (+/-)-clavicipitic acid was achieved in five steps from indole-3-carboxaldehyde.Syntheses of (+/-)-4-cyano-, (+/-)-4-methyl-, and (+/-)-4-hydroxymethyl-6-(2-methyl-1-propen-1-yl)-3,4,5,6-tetrahydro-1H-azepinoindoles are also reported.

A SHORT STEP SYNTHESIS OF CLAVICIPITIC ACIDS FROM 4-CYANOMETHYLINDOLE

4-(3-methyl-1-oxo-2-buten-1-yl)indole (3) was efficiently synthesized from 4-cyanomethyl-1-(p-toluenesulfonyl)indole by alkylation with 2-methyl-2-buten-1-yl tosylate and by successive aerobic oxidation and deprotection of N-tosyl group.The acylindole 3 was used for a short step synthesis of clavicipitic acids (4).

Total Synthesis of the Clavicipitic Acids by an Intramolecular Azide Cycloaddition Strategy

A straightforward total synthesis approach to the structurally unique ergot derailment products, the clavicipitic acids 1 and 2, is described.The synthetic strategy is based on the formation of the seven-membered nitrogen-containing ring of 1 and 2 through an intramolecular azide cycloaddition process.The cycloaddition strategy, which produces solely the imine product 24, does in some sense mimic the proposed biosynthetic pathway to these acids.

TOTAL SYNTHESIS OF (+/-)-CLAVICIPITIC ACIDS I AND II

Ergot alkaloids, clavicipitic acids (3 and 4) were synthesized respectively in racemic forms from 4-(3-oxo-1-butenyl)-indole (5) by way of (6) and (7).Names of clavicipitic acids I and II were proposed for 3 and 4.

IAC REACTIONS IN THE INDOLE SERIES: TOTAL SYNTHESIS OF CLAVICIPITIC ACID

The first total synthesis of clavicipitic acid (1), a derailment product of ergoline biosynthesis, has been accomplished through an intramolecular azide cycloaddition reaction.The 3,4-disubstituted indole required for this work was assembled from indole-4-carboxaldehyde.The single imine generated from cycloaddition reaction was subjected to bromination, dehydrobromination, reduction and hydrolysis to afford clavicipitic acid ( ca. 1:1 mixture of the cis and trans-isomers).