22149-28-6

Usage

Uses

Used in Pharmaceutical Industry:
11-Hydroxytabersonine is used as an intermediate in the production of anti-cancer drugs, specifically for the synthesis of Vincristine, which is effective against various types of cancer. Its role in drug development is crucial due to its contribution to the creation of therapeutic agents that target and combat cancer cells.
Used in Cancer Treatment:
11-Hydroxytabersonine is utilized as a chemotherapeutic agent precursor, playing a significant role in the development of treatments for different cancer types. Its potential to inhibit cell proliferation in cancer cells makes it a valuable component in the fight against malignancies.
Used in Neurodegenerative Disease Research:
In the field of neurodegenerative disease research, 11-Hydroxytabersonine is used as a compound of interest for its potential therapeutic effects. Its presence in studies is aimed at exploring its capacity to mitigate the impacts of neurodegenerative conditions, offering hope for the development of new treatment strategies.
Used in Anti-Inflammatory and Anti-Oxidant Applications:
11-Hydroxytabersonine is employed as an agent with anti-inflammatory and anti-oxidant properties, making it a candidate for use in treatments targeting inflammation and oxidative stress-related conditions. Its multifaceted potential highlights its versatility in pharmaceutical applications beyond cancer treatment.

Upstream product

• 29479-00-3 (-)-tabersonine hydrochloride 
• 287980-11-4 1-[tert-butoxycarbonyl]-3-[2-[[(2,4-dinitrophenyl)sulfonyl][[(2S)-4-ethyl-2,3-dihydro-2-furanyl]methyl]amino]ethyl]-α-methylene-6-[(methanesulfonyl)oxy]-1H-indole-2-acetic acid methyl ester 
• 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 
• 287980-10-3 3-(2-hydroxyethyl)-6-methanesulfonyloxy-2-(1-methoxycarbonylvinyl)indole-1-carboxylic acid tert-butyl ester 
• 287980-09-0 3-(2-acetoxy-ethyl)-2-iodo-6-methanesulfonyloxy-indole-1-carboxylic acid tert-butyl ester 
• 287980-06-7 Acetic acid (E)-3-(4-methanesulfonyloxy-2-nitro-phenyl)-allyl ester 
• 287980-07-8 Acetic acid (E)-3-(2-formylamino-4-methanesulfonyloxy-phenyl)-allyl ester 
• 287980-08-9 Acetic acid (E)-3-(2-isocyano-4-methanesulfonyloxy-phenyl)-allyl ester 
• 287980-03-4 methanesulfonic acid 4-acetylamino-3-nitro-phenyl ester 
• 287980-05-6 Methanesulfonic acid 3-nitro-4-((E)-3-oxo-propenyl)-phenyl ester 
• 1026703-12-7 methanesulfonic acid 4-amino-3-nitro-phenyl ester 
• 287980-04-5 methanesulfonic acid 4-iodo-3-nitro-phenyl ester 
• 22821-80-3 methanesulfonic acid 4-acetamidophenyl ester 
• 24690-19-5 methanesulfonic acid 4-aminophenyl ester 

Downstream Products

• 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 
• 2182-14-1 vindoline 

Relevant academic research and scientific papers

Synthesis of (-)-Melodinine K: A Case Study of Efficiency in Natural Product Synthesis

Efficiency is a key organizing principle in modern natural product synthesis. Practical criteria include time, cost, and effort expended to synthesize the target, which tracks with step-count and scale. The execution of a natural product synthesis, that is, the sum and identity of each reaction employed therein, falls along a continuum of chemical (abiotic) synthesis on one extreme, followed by the hybrid chemoenzymatic approach, and ultimately biological (biosynthesis) on the other, acknowledging the first synthesis belongs to Nature. Starting materials also span a continuum of structural complexity approaching the target with constituent elements on one extreme, followed by petroleum-derived and "chiral pool"building blocks, and complex natural products (i.e., semisynthesis) on the other. Herein, we detail our approach toward realizing the first synthesis of (-)-melodinine K, a complex bis-indole alkaloid. The total syntheses of monomers (-)-tabersonine and (-)-16-methoxytabersonine employing our domino Michael/Mannich annulation is described. Isolation of (-)-tabersonine from Voacanga africana and strategic biotransformation with tabersonine 16-hydroxylase for site-specific C-H oxidation enabled a scalable route. The Polonovski-Potier reaction was employed in biomimetic fragment coupling. Subsequent manipulations delivered the target. We conclude with a discussion of efficiency in natural products synthesis and how chemical and biological technologies define the synthetic frontier.

Total synthesis of (-)-conophylline and (-)-conophyllidine

Double take: The total syntheses of the title compounds were accomplished in a highly convergent manner. The approach features the regio- and diastereoselective Polonovski-Potier-type reaction for the coupling of two aspidosperma skeletons and the formation of the dihydrofuran ring. Troc=2,2,2-trichloroethoxycarbonyl. 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.