88299-06-3

Upstream product

• 88246-05-3 (E)-4-(1-tosyl-1H-indol-4-yl)but-3-en-2-one 
• 55289-35-5 2-bromo-6-nitrotoluene 
• 90481-69-9 3-bromo-2-ethenylaniline 
• 90481-67-7 (2-Bromo-6-nitro-benzyl)-triphenyl-phosphonium; bromide 
• 115-18-4 2-methyl-3-buten-2-ol 
• 90481-72-4 4-bromo-1-[(4-methylphenyl)sulfonyl]-1H-indole 
• 52488-36-5 4-bromo-1H-indole 
• 98-59-9 p-toluenesulfonyl chloride 
• 90481-71-3 N-tosyl-3-bromo-2-ethenylaniline 
• 90481-68-8 1-bromo-2-ethenyl-3-nitrobenzene 
• 603-83-8 3-nitro-o-tolylamine 
• 58579-54-7 3-bromo-2-(bromomethyl)-1-nitrobenzene 
• 112152-12-2 4--3-buten-2-one 
• 4516-90-9 2-methyl-3-buten-1-ol 

Downstream Products

• 33062-26-9 (+/-)-4,6-trans-clavicipitic acid 
• 33062-26-9 (+/-)-4,6-cis-clavicipitic acid 
• 88299-03-0 6-(2-Methyl-propenyl)-5-(toluene-4-sulfonyl)-5,6-dihydro-1H-azepino[5,4,3-cd]indole-4-carboxylic acid methyl ester 
• 88299-02-9 (S)-6-((S)-1,2-Dihydroxy-2-methyl-propyl)-5-(toluene-4-sulfonyl)-5,6-dihydro-1H-azepino[5,4,3-cd]indole-4-carboxylic acid methyl ester 
• 88299-10-9 [[(S)-(1H-Indol-4-yl)-((S)-2,2,5,5-tetramethyl-[1,3]dioxolan-4-yl)-methyl]-(toluene-4-sulfonyl)-amino]-acetic acid methyl ester 
• 88299-11-0 [[(S)-(3-Formyl-1H-indol-4-yl)-((S)-2,2,5,5-tetramethyl-[1,3]dioxolan-4-yl)-methyl]-(toluene-4-sulfonyl)-amino]-acetic acid methyl ester 
• 88298-99-1 (R)-6-((R)-2,2,5,5-Tetramethyl-[1,3]dioxolan-4-yl)-5-(toluene-4-sulfonyl)-5,6-dihydro-1H-azepino[5,4,3-cd]indole-4-carboxylic acid methyl ester 
• 88299-00-7 (R)-6-((R)-5,5-Dimethyl-2-oxo-[1,3]dioxolan-4-yl)-5-(toluene-4-sulfonyl)-5,6-dihydro-1H-azepino[5,4,3-cd]indole-4-carboxylic acid methyl ester 
• 88299-01-8 (R)-6-((R)-5,5-Dimethyl-2-thioxo-[1,3]dioxolan-4-yl)-5-(toluene-4-sulfonyl)-5,6-dihydro-1H-azepino[5,4,3-cd]indole-4-carboxylic acid methyl ester 
• 88299-09-6 4-Methyl-N-{(R)-((R)-2,2,5,5-tetramethyl-[1,3]dioxolan-4-yl)-[1-(toluene-4-sulfonyl)-1H-indol-4-yl]-methyl}-benzenesulfonamide 

Relevant academic research and scientific papers

Rhodium(II)-Catalyzed [4+3] Cyclization of Triazoles with Indole Derivatives and Its Application in the Total Synthesis of (±)-Aurantioclavine

An efficient rhodium(II)-catalyzed [4+3] cyclization reaction of 1-sulfonyl-1,2-3-triazoles and indoles was developed. Azepino[5,4,3- cd]indoles, which are widely distributed in ergot alkaloids with various biological activities, could be obtained in good

Palladium-Catalyzed Reactions in the Synthesis of 3- and 4-Substituted Indoles. Approaches to Ergot Alkaloids

An efficient synthesis of 4-bromo-1-tosylindole (10) based on the Pd(II)-catalyzed cyclization of an o-ethenylaniline p-toluenesulfonamide has been developed.A Pd(0) oxidative addition-olefin insertion-β-hydride elimination cycle converted 10 to a number of 4-substituted 1-tosylindoles.Selective electrophilic substitutions at the 3-position of 10 provided access to the 3-(chloromercurio)- (18) and 3-iodo-1-tosylindoles (22).Transmetalation to palladium and allyl chloride insertion converted 18 to 3-allyl-4-bromo-1-tosylindole (20) which could be cyclized to the benzindoline 21.A Pd(0) oxidative addition-olefin insertion-β-hydride elimination cycle converted the 3-iodo compound 22 to a number of 4-bromo-3-substituted 1-tosylindoles including 24, a potential precursor to optically active tryptophans.

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.