2580-88-3

Usage

Uses

There is no specific information provided about the uses of DL-Eburnamonine in the given materials. However, based on its classification as an alkaloid and its source from Vinca minor, it can be inferred that it may have potential applications in the pharmaceutical industry, possibly for the development of drugs targeting various health conditions. Further research and information would be required to confirm its specific uses and applications.

References

Mokry etal., Experientia, 17,354 (1961) Mokry et al., Chern. Zvesti., 16, 140 (1962) Synthesis: Wenkert, Wickberg., J. Amer. Chern. Soc., 87, 1580 (1965)

Upstream product

• 113973-73-2 ent-12cα-ethyl-1,2,3aα,4,6,7,12,12bβ-decahydrocyclopent<1,2>indolizino<8,7-b>indole-3,4-dione 
• 113974-84-8 ent-1β-ethyl-4-oxo-1,2,3,4,6,7,12,12β-octahydro-1,3-cycloindolo<2,3-a>quinolizin-3β-carboxylic acidmethylester 
• 1395097-86-5 (S,E)-4-((methoxymethoxy)methyl)hex-3-en-2-ol 
• 1395097-87-6 (S,E)-ethyl 3-ethyl-3-((methoxymethoxy)methyl)hex-4-enoate 
• 1395097-89-8 (S,E)-(((3-ethyl-3-((methoxymethoxy)methyl)hex-4-en-1-yl)oxy)methyl)benzene 
• 1395097-88-7 C₁₁H₂₂O₃ 
• 1395097-90-1 (S,E)-2-(2-(benzyloxy)ethyl)-2-ethylpent-3-en-1-ol 
• 1395097-83-2 (S,E)-ethyl 4-((tert-butyldimethylsilyl)oxy)-2-ethylpent-2-enoate 
• 1395097-93-4 (R)-2-allyl-1-((S,E)-1-(benzyloxy)-3-ethylhex-4-en-3-yl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole 
• 1395097-94-5 (1S,12bR)-1-(2-(benzyloxy)ethyl)-1-ethyl-1,4,6,7,12,12b-hexahydroindolo[2,3-a]quinolizine 
• 1395097-95-6 2-((1R,12bR)-1-ethyl-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizin-1-yl)ethanol 
• 1395097-85-4 (S,E)-6-ethyl-8,10,10,11,11-pentamethyl-2,4,9-trioxa-10-siladodec-6-ene 
• 1395097-84-3 C₁₃H₂₈O₂Si 
• 1354568-15-2 C₁₈H₂₁NO₄ 

Downstream Products

• 473-99-4 14,15-dihydroeburnamenin-14-ol 

Relevant academic research and scientific papers

Asymmetric Total Synthesis of Eburnamine and Eucophylline: A Biomimetic Attempt for the Total Synthesis of Leucophyllidine

The first enantiospecific total synthesis of (+)-6 has been achieved employing a Friedl?nder quinoline synthesis as a key step. Asymmetric synthesis of the architecturally complex eburnamine 5 has also been accomplished utilizing an intramolecular acid-mediated cyclization of a carbinol amine lactone moiety. Highlights of the effective modular synthetic strategy include development of the common precursor 4 for the construction of the privileged scaffolds 5 and 6 with an all-carbon quaternary stereocenter utilizing a Johnson-Claisen rearrangement strategy. Attempts have been made to synthesize 1 by the biomimetic coupling of 5 and (+)-6; however, regioisomeric 26 was formed.

The Enantioselective Synthesis of Eburnamonine, Eucophylline, and 16′-epi-Leucophyllidine

A synthetic approach to the heterodimeric bisindole alkaloid leucophyllidine is disclosed herein. An enantioenriched lactam building block, synthesized through palladium-catalyzed asymmetric allylic alkylation, served as the precursor to both hemispheres. The eburnamonine-derived fragment was synthesized through a Bischler–Napieralski/hydrogenation approach, while the eucophylline-derived fragment was synthesized by Friedl?nder quinoline synthesis and two sequential C?H functionalization steps. A convergent Stille coupling and phenol-directed hydrogenation united the two monomeric fragments to afford 16′-epi-leucophyllidine in 21 steps from commercial material.

A Radical Cascade Enabling Collective Syntheses of Natural Products

Natural products have long been important inspirations for the development of chemical methodologies, theories, and technologies, and ultimately, discoveries of new drugs and materials. Chemical syntheses have traditionally yielded individual or small groups of natural products; however, methodology development allowing the synthesis of a large collection of natural products remains scarce. Here, we report an efficient photocatalytic radical cascade method that enables access to libraries of chiral and multiple-ring-fused tetrahydrocarbolinones. The radical cascade can controllably introduce complexity and functionality into products with excellent chemo-, regio-, and diastereoselectivity. The power of this distinct method has been demonstrated by the efficient syntheses of 33 monoterpenoid indole alkaloids belonging to four families.

Enantiospecific total synthesis of indole alkaloids (+)-eburnamonine, (-)-aspidospermidine and (-)-quebrachamine

An enantiospecific total synthesis of indole alkaloids eburnamonine, aspidospermidine and quebrachamine is described from lactic acid. Synthesis of all three alkaloids is accomplished from a single chiral building block. Johnson-Claisen rearrangement of a chiral allyl alcohol is the main feature for the installation of the required quaternary centre.

Total synthesis of (+)-eburnamonine

The enantiospecific total synthesis of vinca alkaloid (+)-eburnamonine is accomplished from l-ethyl lactate. Key feature of the synthesis is the construction of the chiral quaternary center involving a Johnson-Claisen rearrangement and assembly of the pentacyclic core by the Pictet-Spengler reaction and ring-closing metathesis. Georg Thieme Verlag Stuttgart · New York.

Syntheses and Cardiovascular Activity of Stereoisomers and Derivatives of Eburnane Alkaloids

The synthesis of all the possible isomers of the eburnamenine-vincamine type alkaloids 1b, 2a*, 3a and derivatives 4, 8, 9, 10 is described.Structures were determined by 1H- and 13C-NMR spectroscopy including special techniques such as DR, DEPT, DNOE, and 2D-HSC.In contrast to the known cerebrovascular effects of cis-(3S,16S) compounds, trans-(3S,16R) derivatives show a significant peripheral vasodilator effect. Key Word: Eburnanes / Alkaloids / Cardiovascular effects / Indoloquinolizines

Reactions with indole derivatives-LV. An enantiodivergent route to both vincamine enantiomers

The enantioselective synthesis of the tetracyclic lactam 4 is reported which by enantiodivergent techniques is converted into (+)- as well as (-)-vincamine via the corresponding eburnamonine enantiomers.

Total Synthesis of (-)-Kopsinilam, (-)-Kopsinine, and the Bis-indole Alkaloids (-)-Norpleiomutine and (-)-Pleiomutine

The racemic tetracyclic amine (5) was resolved and converted into (-)-kopsinine (16); subsequent coupling to (-)-eburnamine (2) gave (-)-norpleiomutine (4).

Process for the preparation of eburnamonine derivatives

The invention relates to a new process for the preparation of eburnamonine derivatives of the general Formula I STR1 (wherein R1 is an alkyl group having 1-6 carbon atoms) and optical and geometrical isomers thereof which comprises reacting a hydroxyimino-octahydro-indolo[2,3-a]quinolizine derivative of the general Formula II STR2 (wherein R1 is as stated above and R2 stands for an alkyl group having 1-6 carbon atoms being identical with or different from R1, or a hydrogen atom) or an acid addition salt thereof in an organic protic solvent or solvent mixture with an inorganic base, optionally under the addition of water or an aqueous mineral acid, at a temperature between 60° C. and 200° C. The compounds of the present invention are known drugs having blood pressure decreasing and cerebral vasodilatatory effect. The advantage of the process of the present invention is that it is readily feasible on industrial scale too, provides isomer-free pure products with high yield and requires the use of readily available simple starting materials.