22149-28-6

Basic information

• Product Name: 11-Hydroxytabersonine
• Synonyms: 11-Hydroxytabersonine;16-hydroxytabersonine
• CAS NO: 22149-28-6
• Molecular Formula: C21H24N2O3
• Molecular Weight: 352.43
• Mol File: 22149-28-6.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 11-Hydroxytabersonine(CAS DataBase Reference)
• NIST Chemistry Reference: 11-Hydroxytabersonine(22149-28-6)
• EPA Substance Registry System: 11-Hydroxytabersonine(22149-28-6)

Safety Data

• Hazardous Substances Data: 22149-28-6(Hazardous Substances Data)

Usage

General Description

11-Hydroxytabersonine is a chemical compound that is derived from the Tabersonine alkaloid found in certain plants, including the medicinal plant Voacanga africana. It is an intermediate in the biosynthesis of the anti-cancer drug Vincristine, which is used in the treatment of various types of cancer. 11-Hydroxytabersonine has been the subject of research for its potential therapeutic properties, including its ability to inhibit cell proliferation in cancer cells and its potential in the treatment of neurodegenerative diseases. Studies have also shown that 11-Hydroxytabersonine has anti-inflammatory and anti-oxidant properties, making it a compound of interest for further investigation in the development of new pharmaceuticals.

Upstream product

• 29479-00-3 (-)-tabersonine hydrochloride 
• 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 
• 20455-07-6 p-nitrophenyl methanesulfonate 
• 287980-14-7 (-)-11-Mesyloxytabersonine 
• 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 

Downstream Products

• 2182-14-1 vindoline 
• 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 

Relevant articles and documents

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.

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.