468-53-1 Usage
Description
Mesembrine is an alkaloid that occurs naturally in its (-)-form and is known for its serotonin-uptake inhibitory properties. It is found in the plant Sceletium tortuosum, which is native to Southwest Africa and has been traditionally used for its mood-enhancing and adaptogenic effects.
Uses
Used in Pharmaceutical Industry:
Mesembrine is used as a pharmaceutical compound for its ability to inhibit serotonin uptake, which can help in the treatment of mood disorders and anxiety. Its natural occurrence and traditional use in Southwest Africa highlight its potential as a therapeutic agent for mental health.
Used in Traditional Medicine:
In the context of traditional medicine, Mesembrine is used as an ingredient in the preparation of Channa, a drug native to Southwest Africa. Its mood-enhancing and adaptogenic properties make it a valuable component in traditional healing practices.
Used in Nutraceutical Industry:
Given its serotonin-uptake inhibitory properties, Mesembrine can also be used as a nutraceutical ingredient to support mental well-being and promote a sense of calm and relaxation. It can be incorporated into dietary supplements and functional foods to help individuals manage stress and improve mood.
Synthesis
Michael addition of 3,4-dimethoxyphenylacetonitrile 17 to methyl acrylate 18 using
10% aq. NaOH under PTC conditions afforded double Michael adduct 19 in 75% yield.
Alternatively, compound 19 was obtained using catalytic Triton-B in refluxing CH3CN in
quantitative yields! Dieckmann condensation of 19 using NaH in DME furnished βketoester, which was demethoxycarbonylated using Krapcho’s method to obtain ketone 20.
Ketone 20 was protected as dioxolane with 2,2-dimethyl-1,3-propanediol in refluxing
benzene using PPTS as a catalyst.Nitrile was then reduced with DIBAL in DCM at 0 o
C to obtain aldehyde, which
was converted to olefin 21 with methylenetriphenylphosphorane employing Wittig
reaction. Olefin 21 was then subjected to hydroboration with BMS complex, followed by
alkaline work-up to give alcohol, which was mesylated and the resultant mesylate was
further treated with 30% aq. MeNH2 solution in a sealed tube at 100 o
C to yield amine,
which was protected as benzyl carbamate. Dioxolane was then hydrolysed by refluxing in
an acetone-water mixture (1:1) with a drop of conc. H2SO4 to obtain ketone 22. Silyl enol
ether of the resultant ketone 22 was prepared, which was subsequently brominated with
NBS to give α-bromoketone, which upon dehydrobromination with LiBr and Li2CO3 in hot
DMF provided enone 23. The carbamate was unmasked with BF3·OEt2 in the presence of
excess of Me2S to give the target molecule 16 .
Check Digit Verification of cas no
The CAS Registry Mumber 468-53-1 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 4,6 and 8 respectively; the second part has 2 digits, 5 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 468-53:
(5*4)+(4*6)+(3*8)+(2*5)+(1*3)=81
81 % 10 = 1
So 468-53-1 is a valid CAS Registry Number.
InChI:InChI=1/C17H23NO3/c1-18-9-8-17(7-6-13(19)11-16(17)18)12-4-5-14(20-2)15(10-12)21-3/h4-5,10,16H,6-9,11H2,1-3H3/t16-,17-/m1/s1
468-53-1Relevant articles and documents
Palladium-catalyzed asymmetric direct intermolecular allylation of α-aryl cyclic vinylogous esters: Divergent synthesis of (+)-oxomaritidine and (?)-mesembrine
Wang, Wei,Dai, Jun,Yang, Qiqiong,Deng, Yu-Hua,Peng, Fangzhi,Shao, Zhihui
, p. 920 - 924 (2021/02/16)
We demonstrate that α-aryl cyclic vinylogous esters are competent substrates in the direct intermolecular Pd-catalyzed asymmetric allylic alkylation, enabling a straightforward enantioselective synthesis of 6-allyl-6-aryl-3-ethoxycyclohex-2-en-1-ones, common motifs embedded in numerous structurally diverse natural products. As an initial demonstration of the utility of this protocol, the first catalytic enantioselective total synthesis of (+)-oxomaritidine and an improved five-step catalytic enantioselective synthesis of (?)-mesembrine have been completed divergently.
Asymmetric Synthesis of Remote Quaternary Centers by Copper-Catalyzed Desymmetrization: An Enantioselective Total Synthesis of (+)-Mesembrine
Bokka, Apparao,Mao, James X.,Hartung, John,Martinez, Steven R.,Simanis, Justin A.,Nam, Kwangho,Jeon, Junha,Shen, Xiaoqiang
supporting information, p. 5158 - 5162 (2018/09/13)
Catalytic asymmetric syntheses of remote quaternary stereocenters have been developed by copper-catalyzed 1,4-hydrosilylation of ?,?-disubstituted cyclohexadienones. A variety of cyclohexenones have been synthesized in good yield and excellent enantioselectivity. Versatile 2-silyloxy diene intermediates bearing ?,?-disubstituted all carbon stereogenic centers can be isolated from the mild reaction conditions. The utility of this strategy is exemplified in a catalytic asymmetric total synthesis of (+)-mesembrine.
Total Synthesis of (+)-Mesembrine Applying Asymmetric Gold Catalysis
Spittler, Michael,Lutsenko, Kiril,Czekelius, Constantin
, p. 6100 - 6105 (2016/07/26)
The total synthesis of enantiomerically pure (+)-mesembrine is described. The central pyrrolidine moiety incorporating a quaternary, all-carbon-substituted stereocenter was constructed employing an asymmetric gold-catalyzed cycloisomerization of a 1,4-diynamide.
