19074-77-2

Usage

Uses

Used in Pharmaceutical Industry:
(5α,12β,19α)-2,3-Didehydro-1-methylaspidospermidine-3-carboxylic acid methyl ester is used as a pharmaceutical compound for its potential therapeutic applications. The alkaloid's unique structure and properties make it a promising candidate for the development of new drugs and treatments.
Used in Chemical Research:
In the field of chemical research, (5α,12β,19α)-2,3-Didehydro-1-methylaspidospermidine-3-carboxylic acid methyl ester serves as a valuable subject for studying the properties and interactions of alkaloids. Its synthesis and structural confirmation contribute to the understanding of the chemical behavior of similar compounds and can lead to the discovery of new synthetic methods and applications.
Used in Drug Development:
(5α,12β,19α)-2,3-Didehydro-1-methylaspidospermidine-3-carboxylic acid methyl ester is utilized in drug development as a starting material or a key intermediate for the synthesis of novel therapeutic agents. Its unique structural features can be exploited to design and develop new drugs with improved efficacy and selectivity.
Used in Quality Control and Standardization:
This alkaloid can be employed in the quality control and standardization of natural products and pharmaceuticals derived from Vinca minor L. or other related plants. By establishing a reference standard for (5α,12β,19α)-2,3-Didehydro-1-methylaspidospermidine-3-carboxylic acid methyl ester, it becomes possible to ensure the consistency, purity, and potency of related products in the market.

References

Kokry, Dubravkova, Sefecovic.,Experientia, 18,564 (1962)Mokryetal., ibid, 19,311 (1963)Zachystalova, Strouf, Trojanek., Chern. & Ind., 610 (1963)Synthesis: Kutney et al., J. Amer. Chern. Soc., 90,3891 (1968)

Upstream product

• 18374-17-9 (±)-vincadifformine 
• 74-88-4 methyl iodide 
• 53956-14-2 1-(2-(1H-indol-3-yl)ethyl)-3-ethylpiperidin-2-one 
• 165385-85-3 (+/-)-3-ethyl-2-piperidone 
• 102487-94-5 {3-[2-(3-Ethyl-piperidin-1-yl)-ethyl]-1H-indol-2-yl}-acetic acid methyl ester 
• 219874-01-8 16,17,15,20-tetrahydrosecodin-17-ol N-oxide 
• 102487-92-3 Benzoic acid 3-[2-(3-ethyl-piperidin-1-yl)-ethyl]-1H-indol-2-ylmethyl ester 
• 102487-95-6 (E)-2-{3-[2-(3-Ethyl-piperidin-1-yl)-ethyl]-1H-indol-2-yl}-3-hydroxy-acrylic acid methyl ester 
• 102487-90-1 3-[2-(5-Ethyl-2-oxo-piperidin-1-yl)-ethyl]-1H-indole-2-carboxylic acid ethyl ester 
• 102487-93-4 {3-[2-(3-Ethyl-piperidin-1-yl)-ethyl]-1H-indol-2-yl}-acetonitrile 
• 102487-91-2 {3-[2-(3-Ethyl-piperidin-1-yl)-ethyl]-1H-indol-2-yl}-methanol 
• 28423-88-3 16,17,15,20-tetrahydrosecodin-17-ol 
• 77785-14-9 ethyl 3-<2-(5-ethyl-1,2,3,4-tetrahydro-2-oxo-1-pyridinyl)ethyl>-2-indolecarboxylate 

Relevant academic research and scientific papers

Total synthesis of natural (-)- and ent-(+)-4-desacetoxy-6,7- dihydrovindorosine and natural and ent-minovine: Oxadiazole tandem intramolecular diels-alder/1,3-dipolar cycloaddition reaction

(Chemical Equation Presented) Efficient and unusually concise total syntheses of both enantiomers of the Aspidosperma alkaloids 4-desacetoxy-6,7- dihydrovindorosine (12) and minovine (1) are detailed. A tandem intramolecular Diels-Alder/1,3-dipolar cycloaddition reaction of the 1,3,4-oxadiazole 8, in which three new rings, four new C-C bonds, and five stereocenters are formed, is a key step in the sequence. The availability of optically active material permitted an assessment of the enantiomeric integrity of minovine and the source of its reported unusual optical rotation.

Expeditious and Divergent Total Syntheses of Aspidosperma Alkaloids Exploiting Iridium(I)-Catalyzed Generation of Reactive Enamine Intermediates

A new approach for the divergent total syntheses of (±)-vincaminorine, (±)-N-methylquebrachamine, (±)-quebrachamine, (±)-minovine and (±)-vincadifformine, each in less than 10 linear steps starting from a single δ-lactam building block, is reported. Key to our route design is the late-stage generation of reactive enamine functionality from stable indole-linked δ-lactams via a highly chemoselective iridium(I)-catalyzed reduction. The efficiently formed secodine intermediates subsequently undergo either a formal Diels–Alder cycloaddition or a competitive Michael addition/reduction to access aspidosperma-type alkaloids in excellent diastereoselectivities. Product selectivity could be controlled by changing the indole N-protecting group in the reductive cyclization precursors. An asymmetric variant of this synthetic strategy for the synthesis of (+)-20-epi-ibophyllidine is also described.

Total synthesis of (-)- and ent-(+)-vindoline and related alkaloids

A concise 11-step total synthesis of (-)- and ent-(+)-vindoline (3) is detailed based on a unique tandem intramolecular [4 + 2]/[3 + 2] cycloaddition cascade of a 1,3,4-oxadiazole inspired by the natural product structure, in which three rings and four C-C bonds are formed central to the characteristic pentacyclic ring system setting all six stereocenters and introducing essentially all the functionality found in the natural product in a single step. As key elements of the scope and stereochemical features of the reaction were defined, a series of related natural products of increasing complexity were prepared by total synthesis including both enantiomers of minovine (4), 4-desacetoxy-6,7-dihydrovindorosine (5), 4-desacetoxyvindorosine (6), and vindorosine (7) as well as /V-methylaspidospermidine (11). Subsequent extensions of the approach provided both enantiomers of 6,7-dihydrovindoline (8), 4-desacetoxyvindoline (9), and 4-desacetoxy-6,7-dihydrovindoline (10).

SYNTHESIS OF VINCA ALKALOIDS AND RELATED COMPOUNDS. XXV. A NEW APPROACH TO (+/-)-TETRAHYDROSECODIN-17-OL, (+/-)-TETRAHYDROSECODINE, (+/-)-VINCADIFFORMINE, (+/-)-ψ-VINCADIFFORMINE AND (+/-)-MINOVINE

Starting from 1 the syntheses of the title compounds were achieved using Polonovski reaction of 7 as the key step.