55529-55-0

Usage

Uses

Used in Pharmaceutical Industry:
17β-Hydroxy-19α-methyl-18-oxayohimban-16α-carboxylic acid methyl ester is used as a pharmaceutical compound for its potential therapeutic properties. 17β-Hydroxy-19α-methyl-18-oxayohimban-16α-carboxylic acid methyl ester's unique structure may allow it to interact with specific biological targets, making it a candidate for the development of new drugs.
Used in Chemical Research:
In the field of chemical research, 17β-Hydroxy-19α-methyl-18-oxayohimban-16α-carboxylic acid methyl ester serves as a valuable subject for studying the synthesis, reactivity, and potential applications of complex organic molecules. Its unique structure can provide insights into the development of new synthetic methods and the exploration of novel chemical reactions.
Used in Drug Delivery Systems:
Similar to gallotannin, 17β-Hydroxy-19α-methyl-18-oxayohimban-16α-carboxylic acid methyl ester could be employed in drug delivery systems to enhance its bioavailability and therapeutic outcomes. By incorporating the compound into various carriers, such as organic or metallic nanoparticles, its delivery and efficacy against specific targets can be improved.

References

Bombardelli et al., Fitoterapia, 45, 183 (1974)

Upstream product

• 483-04-5 ajmalicine 
• 2883-99-0 3-Acetyl-1-[2-(1H-indol-3-yl)-ethyl]-pyridinium; bromide 
• 60339-88-0 rac-19-oxo-(15βH)-17-nor-coryn-20-ene-16,16-dicarboxylic acid dimethyl ester 

Downstream Products

• 483-03-4 tetrahydroalstonine 
• 483-03-4 DL-Akuammigin 

Relevant academic research and scientific papers

HETEROYOHIMBINE ALKALOID SYNTHESIS

Preparation of the heteroyohimbine analogues 6 and 7 and a new short stereoselective total synthesis of (+/-)-3-iso-19-epiajmalicine 12 are described.

STEREOSELECTIVE TOTAL SYNTHESIS OF (+/-)-3-ISO-19-EPIAJMALICINE

A new stereoselective three-step total synthesis of (+/-)-3-iso-19-epiajmalicine 4 starting from the easily accessible compound 1 is described.

Heteroyohimbine Alkaloids. Stereospecific Conversion of Ajmalicine into 19-Epiajmalicine

An efficient four-step sequence to 19-epiajmalicine, a rare heteroyohimbane alkaloid, which requires mild conditions and utilises ajmalicine as an easily accessible starting material, is described.

GENERAL METHODS OF SYNTHESIS OF INDOLE ALKALOIDS - 14. SHORT ROUTES OF CONSTRUCTION OF YOHIMBOID AND AJMALICINOID ALKALOID SYSTEMS AND THEIR 13C NUCLEAR MAGNETIC RESONANCE SPECTRAL ANALYSIS.

Conceptually new schemes of synthesis of indole alkaloids are introduced. The yohimboid ring system is constructed by the sequential treatment of 1-tryptophyl-3-( beta -ketobutyl)pyridinium bromide with base and acid. Hydrogenation of the product yields d,l-pseudoyohimbone. The ajmalicinoid ring system is formed by the exposure of 1-tryptophyl-3-acetylpyridinium bromide to sodio dimethyl malonate and then to acid, followed by hydrogenation. Subsequent reduction and dehydration of the products lead to the racemates of the alkaloids tetrahydroalstonine and akuammigine as well as isomers of ajmalicine. Shifts of specific carbons are found to be of stereochemically diagnostic value.