549-84-8

Usage

Uses

Used in Pharmaceutical Industry:
Methyl (16alpha,17beta)-17-hydroxyyohimban-16-carboxylate is utilized as a key component in the development of therapeutic compounds, particularly for the treatment of erectile dysfunction. Its efficacy in this area is well-documented, making it a valuable asset in the management of this condition.
Used in Dietary Supplements:
In addition to its pharmaceutical applications, methyl (16alpha,17beta)-17-hydroxyyohimban-16-carboxylate is also found in dietary supplements, where it is used to aid in weight loss. Its role in this context is to support the body's metabolic processes and enhance fat burning, contributing to overall weight management.
However, it is important to note that the use of methyl (16alpha,17beta)-17-hydroxyyohimban-16-carboxylate is not without its risks. It has been associated with side effects such as rapid heart rate, high blood pressure, and overstimulation. Due to these potential adverse effects, its use is typically recommended under medical supervision to ensure safety and effectiveness.

Upstream product

• 146-48-5 Yohimbine 
• 115182-50-8 17β-methoxy-yohimban-16α-carboxylic acid methyl ester 
• 106861-83-0 17β-acetoxy-yohimban-16α-carboxylic acid 
• 51598-49-3 (-)-Δ^15,16-didehydroyohimbinone 
• 2671-57-0 (+)-yohimbinone 
• 295790-93-1 (-)-3-iso-19,20-dehydro-β-yohimbine 
• 549-82-6 pseudo-β-yohimbine 
• 19351-63-4 secologanin 
• 27856-66-2 O,O,O,O-tetraacetylsecologaninn 
• 79409-45-3 Methyl (2S,3R,4S)-4-(1,3-Dioxolan-2-ylmethyl)-2-(β-D-glucopyranosyloxy)-3,4-dihydro-3-vinyl-2H-pyran-5-carboxylate 
• 79409-46-4 Methyl (2S,3R,4S)-4-(1,3-Dioxolan-2-ylmethyl)-3,4-dihydro-2-(2,3,4,6-tetraacetyl-β-D-glucopyranosyloxy)-3-vinyl-2H-pyran-5-carboxylate 
• 120132-02-7 (1R,2R,6R)-2-[1,3]Dioxolan-2-ylmethyl-3-formyl-6-hydroxy-cyclohex-3-enecarboxylic acid methyl ester 
• 297131-94-3 (1R,2R,6R)-2-[1,3]Dioxolan-2-ylmethyl-6-hydroxy-3-{[2-(1H-indol-3-yl)-ethylamino]-methyl}-cyclohex-3-enecarboxylic acid methyl ester 
• 54725-64-3 18,19-didehydroyohimban-17-one 

Downstream Products

• 2671-57-0 (+)-yohimbinone 
• 146-48-5 Yohimbine 

Relevant academic research and scientific papers

Enantiospecific synthesis of (-)-3-iso-19,20-dehydro-β-yohimbine from secologanin: A route to normal and pseudo stereoisomers of yohimbine

Hydrolysis of secologanin ethylene acetal at pH 7 resulted in stereoselective aldol cyclisation to a cyclohexene aldehyde, which, on reductive amination and cyclisation with tryptamine afforded (-)-3-iso-19,20- dehydro-β-yohimbine, converted into various normal and pseudo isomers of yohimbine. (C) 2000 Elsevier Science Ltd.

Symmetry-driven synthesis of indole alkaloids: Asymmetric total synthesis of (+)-yohimbine, (-)-yohimbone, (-)-yohimbane, and (+)-alloyohimbane

Total asymmetric syntheses of the target alkaloids are reported. The syntheses involve the preparation of enantiomerically pure (S,S)-1,3,3a,4,7,7a-hexahydro-2(H)-inden-2-one 7 and its meso isomer 5. Each ketone is then converted into a ring-expanded lactam using an oxaziridine synthesis/rearrangement protocol. The applications of Bischler-Napieralski ring constructions along with appropriate functional group transformations afford enantiomerically enriched alloyohimbane or yohimbane from the meso-or C2-symmetric ketones, respectively. A cis-5,6-diacetoxy compound (18) derived from the (S,S)-ketone served as the starting material for the total syntheses of the more highly functionalized alkaloids. Accordingly, a site-specific insertion of the indole-containing side chain was accomplished via stereoselective formation of an oxaziridine followed by its stereospecific rearrangement. The selectivity of this sequence allowed for the differentiation of alcohols at C-17 and C-18 (yohimbine numbering) and the synthesis of Δ18,19-yohimbone. This α,β-unsaturated ketone was converted into either (-)-yohimbone or (+)-yohimbine using standard chemistry.

Total Syntheses of Yohimbe Alkaloids, with Stereoselection for the Normal, Allo, and 3-Epiallo Series, Based on Annelations of 4-Methoxy-1,2-dihydropyridones

N--2,3-dihydro-4-pyridone (31) was generated in two steps (77percent yield) from tryptamine and N-methyl-4-piperidone methiodide.Its cyclization (90percent yield) and oxidation (91percent yield) provided the tetracyclic analogue 32.O-Methylation and Robinson-type annelation of these vinylogous lactams (the latter in form of its Na-carbamate) furnished the dienones 38 (64percent) and 43 (90percent).Further elaboration by cyclization and/or reduction reactions selectively provided the 15,16-didehydroyohimbinones 7 and 44.Their reductions then led to yohimbinone (52, 20percent overall yield from tryptamine), alloyohimbinone (11, 19percent overall yield), and 3-epi-alloyohimbinone (10, 23percent overall yield), which led to yohimbine (3), β-yohimbine (9), 3-epi-alloyohimbine (53), and 3-epi-17-epi-alloyohimbine (54).