1617-90-9Relevant articles and documents
Ozonation in Alkaloid Chemistry: a Mild and Selective Conversion of Vincadifformine into Vincamine
Danieli, Bruno,Lesma, Giordano,Palmisano, Giovanni,Gabetta, Bruno
, p. 908 - 909 (1981)
Vincamine has been obtained in a 'one-pot' method by ozonation of vincadifformine.
SYNTHESIS OF VINCA ALKALOIDS AND RELATED COMPOUNDS. PART 18. STEREOCHEMICAL INVESTIGATIONS ON SOME INTERMEDIATES LEADING TO (+)-VINCAMINE
Szabo, Lajos,Kolonits, Pal,Kalaus, Gyoergy,Szantay, Csaba,Kalman, Alajos,et al.
, p. 1629 - 1636 (1984)
The C-2' absolute configrations of hydroxy esters (1) and (2) have been determined by X-ray analysis.The absolute configurations at C-15 of several compounds with the E-homoeburnane skeleton and the relative configurations at C-14 and -15 of compound (8) have been elucidated.The dominant conformation of compounds (3)-(7) have been established on the basis of 13C n.m.r. and c.d.spectroscopic results.A new method has been elaborated for the preparation of oxime (10), a compound of importance in the synthesis of Vinca alkaloids.
METHYLENE-INDOLINES, INDOLENINES ET INDOLENIUMS-XIII; L'HYDROXY-16 DEHYDRO-1 VINCADIFFORMINE, INTERMEDIAIRE DANS LE REARRANGEMENT BIOMIMETIQUE DE LA VINCADIFFORMINE EN VINCAMINE
Hugel, G.,Massiot, G.,Levy, J.,Men, J. Le
, p. 1369 - 1376 (1981)
The title compound is a crucial intermediate in the biomimetic conversion of vincadifformine 1 into vincamine 7.Its configuration at C-16 is established by a combination of chemical and spectroscopic evidence.Iodine oxidation converts 14 into the bridged lactam 18, thus proving a β configuration for the hydroxy group at C-16.The same reaction applied to vindoline 19 gives 21 identical with one of the compounds obtained by microbiological transformation of 19.The 13C NMR spectra of derivatives 3 and 8 (obtained by oxidation of vincadifformine) show that oxidation proceeds with introduction of the substituent at C-16, with a β configuration.The alcohol 3 however, posesses a different conformation due to strong hydrogen bonding with N-4.
Alpneumines A-H, new anti-melanogenic indole alkaloids from Alstonia pneumatophora
Koyama, Koichiro,Hirasawa, Yusuke,Hosoya, Takahiro,Hoe, Teh Chin,Chan, Kit-Lam,Morita, Hiroshi
, p. 4415 - 4421 (2010)
Eight new indole alkaloids, alpneumines A-H (1-8) were isolated from the Malaysian Alstonia pneumatophora (Apocynaceae) and their structures were determined by MS and 2D NMR spectroscopic methods. Alpneumines E and G (5 and 7), vincamine, and apovincamine showed anti-melanogenesis in B16 mouse melanoma cells.
Synthesis of vinca alkaloids and related compounds, XV. A new synthetic route to (+)-vincaminic and (+)-apovincaminic esters
Szabo,Kalaus,Szantay
, p. 629 - 638 (1983)
Esters of types 7 and 8, possessing excellent vasodilating effects, have been prepared. A method has been found for the resolution of methyl ester 7c. A new method is described for the preparation of the lactam (+)-10 and its conversion to the oxime (+)-11, from which (+)-vincamine (1a) and the (+)-apovincaminic esters 2a,b were synthesized.
Synthesis of vinca alkaloids and related compounds LX. A simple transformation of apovincamine into vincamine
Moldvai, Istvan,Szantay Jr., Csaba,Rissanen, Kari,Szantay, Csaba
, p. 4999 - 5008 (1992)
The 15α-chloro-vincamine derivative 2 was prepared and proved to be key intermediate of a two-step transformation of apovincamine into vincamine. The structure of 2 was established via detailed NMR and X-ray investigations.
Enantioselective total synthesis of (+)-vincamine
Liu, Hengmao,Liu, Xiao-Yu,Qin, Yong,Song, Hao,Wang, Rui,Xue, Fanglin,Zhang, Dan
, (2021/10/06)
A catalytic asymmetric total synthesis of (+)-vincamine is presented. Key features of the synthesis include a Pd-catalyzed enantioselective decarboxylative allylation to form the C20 quaternary stereogenic center and a stereoselective iminium reduction to install the critical cis-C20/C21 relative stereochemisty.
Intermediate, preparation method and application of intermediate in synthesis of vincamine
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, (2021/09/01)
The invention relates to the technical field of chemical drug synthesis, and discloses an intermediate, a preparation method and application of the intermediate in synthesis of vincamine. A modular synthesis strategy is adopted, and a compound 1 with a D ring structure and a C20 quaternary carbon center and a tryptophol derivative 7 (namely the compound 7) with an indole ring are adopted as synthesis blocks for synthesis. The synthesis method is efficient; each step of the synthesis route is simple in reaction; the used reagent and solvent are cheap and easy to obtain; the operation is simple and convenient; the yield is high; and large-scale production is easy.
Preparation method of vincamine
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Paragraph 0044-0047, (2021/04/21)
The invention provides a green preparation method of vincamine, which comprises the following steps: (1) reduction: introducing a tabersonine methanol solution and hydrogen into a micro-channel reactor through a charging pump to react, and filtering, concentrating and extracting the reaction solution twice after the reaction is finished, thereby obtaining an extracting solution; (2) oxidation: catalyzing an organic phase in the extraction liquid in the step (1) by using peroxy acid to carry out oxidation reaction, neutralizing by using a sodium bicarbonate solution after the reaction is finished, extracting and concentrating; and (3) rearrangement: dissolving the concentrated solid obtained in the step (2) with ethanol, rearranging in the presence of a catalyst, adjusting the pH value after the reaction is completed, filtering, washing and crystallizing the filter cake, and separating out the solid, namely vincamine. The preparation method is safe, environmentally friendly and capable of achieving continuous production, the product purity is 99% or above, automatic equipment can be adopted for continuous production, and the industrial production efficiency is improved.
Preparation method of high-purity vinpocetine (by machine translation)
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Paragraph 0041; 0043-0044; 0051-0056, (2020/04/17)
The preparation method, of the high-purity vinpocetine :S1. comprises, following steps: preparing vinpocstine, by dissolving; in toluene as a solvent; in toluene as a solvent ;S2. and carrying out an ester exchange reaction, to obtain the intermediate vinpocstine nitrogen oxide, in a toluene as a solvent, and carrying out an ester exchange reaction to obtain a product impurity at least ;S3. purity S2 and, % by mass of a solvent . The preparation method of the vinpocstine nitrogen oxide reaction solution in step, is adopted as a catalyst for carrying out an ester exchange reaction to obtain a long spring cavoniflorac sodium/vinpocstine . The process production operation is, simple, avoids the high, 99.9% toxicity reagent, to obtain a, long spring cavonift, nitrogen oxide reaction, solution to, obtain a product, impurity at a time of acid. (by machine translation)
