19074-77-2

Basic information

• Product Name: (5α,12β,19α)-2,3-Didehydro-1-methylaspidospermidine-3-carboxylic acid methyl ester
• Synonyms: (5α,12β,19α)-2,3-Didehydro-1-methylaspidospermidine-3-carboxylic acid methyl ester;Minovin;Minovine
• CAS NO: 19074-77-2
• Molecular Formula: C22H28N2O2
• Molecular Weight: 352.46992
• Mol File: 19074-77-2.mol
• Article Data: 7

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (5α,12β,19α)-2,3-Didehydro-1-methylaspidospermidine-3-carboxylic acid methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (5α,12β,19α)-2,3-Didehydro-1-methylaspidospermidine-3-carboxylic acid methyl ester(19074-77-2)
• EPA Substance Registry System: (5α,12β,19α)-2,3-Didehydro-1-methylaspidospermidine-3-carboxylic acid methyl ester(19074-77-2)

Safety Data

• Hazardous Substances Data: 19074-77-2(Hazardous Substances Data)

Usage

Description

A further alkaloid isolated from Vinca minor L., this base is possibly optically inactive, the specific rotation reported being [α]D 00 ± 2° (c 1.0, EtOH). The ultraviolet spectrum in EtOH has a broad absorption maximum at 338 mil and an inflexion at 310 mil. The structure has been confirmed by the synthesis of the (±)-form.

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

• 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 
• 473742-75-5 methyl 5-{(4-ethylpent-4-enoyl)-[2-(1-methyl-1H-indol-3-yl)ethyl]amino}-1,3,4-oxadiazole-2-carboxylate 
• 7518-21-0 2-(1-methyl-1H-indol-3-yl)ethylamine 

Relevant articles and documents

Vincadifformine and minovine, 2 additional racemic alkaloids from Vinca minor L.

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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).

Studies on indole alkaloid biosynthesis.

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