287980-11-4

Upstream product

• 1576-86-9 2-pentenal 
• 22821-80-3 methanesulfonic acid 4-acetamidophenyl ester 
• 410071-80-6 (2S)-4-ethyl-2-hydroxy-6-phenylhex-5-enenitrile 
• 410071-99-7 (2S)-4-ethyl-5-hydroxytetrahydrofuran-2-carbonitrile 
• 410071-81-7 (S)-4-ethyl-2,3-dihydrofuran-2-carbonitrile 
• 439590-21-3 3-ethyl-5-phenyl-4-pentenal 
• 1656-44-6 2,4-dinitrobenzenesulfonyl chloride 
• 221903-32-8 N-((2S)-4-ethyl-2,3-dihydrofuran-2-ylmethyl)-2,4-dinitrobenzenesulfonamide 
• 287980-10-3 3-(2-hydroxyethyl)-6-methanesulfonyloxy-2-(1-methoxycarbonylvinyl)indole-1-carboxylic acid tert-butyl ester 
• 410071-83-9 methanesulfonic acid 4-[(Z)-3-hydroxypropenyl]-3-isothiocyanatophenyl ester 
• 410072-02-5 6-methanesulfonyloxy-2-(1-methoxycarbonylvinyl)-3-[2-(tetrahydropyran-2-yloxy)ethyl]indole-1-carboxylic acid tert-butyl ester 
• 410071-85-1 2-{6-methanesulfonyloxy-3-[2-(tetrahydropyran-2-yloxy)ethyl]-1H-indol-2-yl}malonic acid benzyl ester methyl ester 
• 410071-84-0 2-{5-methanesulfonyloxy-2-[(Z)-3-(tetrahydropyran-2-yloxy)propenyl]-phenylthiocarbamoyl}malonic acid benzyl ester methyl ester 
• 410072-00-3 methanesulfonic acid 3-isothiocyanato-4-[(Z)-3-(tetrahydropyran-2-yloxy)propenyl]phenyl ester 

Downstream Products

• 2182-14-1 vindoline 
• 22149-28-6 11-hydroxytabersonine 
• 3633-92-9 (3aR,3a¹R,4R,5S,5aR,10bR)-methyl 3a-ethyl-4,5-dihydroxy-8-methoxy-6-methyl-3a,3a¹,4,5,5a,6,11,12-octahydro-1H-indolizino-[8,1-cd]carbazole-5-carboxylate 
• 502423-37-2 2-(3-{2-[(2,4-dinitro-benzenesulfonyl)-(4-ethyl-5-hydroxy-tetrahydro-furan-2-ylmethyl)-amino]-ethyl}-6-methanesulfonyloxy-1H-indol-2-yl)-acrylic acid methyl ester 

Relevant academic research and scientific papers

Stereocontrolled total synthesis of (+)-vinblastine

A stereocontrolled total synthesis of (+)-vinblastine was accomplished, featuring preparations of the two indole units by means of a novel indole synthesis via radical cyclization of thioanilide, and a stereoselective coupling of these units. Copyright

An efficient total synthesis of (-)-vindoline

A highly efficient total synthesis of the title compound is described. Our synthesis features a highly efficient preparation of the key intermediate 11 using our novel indole synthesis methodology. A novel amine protecting protocol by means of 2,4-dinitrobenzenesulfonamides has been developed to ensure the formation of the elusive secodine-type intermediate 15 under very mild conditions.