- Synthetic method of lobeline hydrochloride
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The invention relates to the technical field of medicine synthesis, and particularly discloses a method for synthesizing lobeline hydrochloride. The method comprises the following steps: performing acylation reaction on ethyl acetoacetate and benzoyl chloride serving as raw materials in the presence of NaOH, NH4Cl and the like, performing hydrolysis reaction on the obtained ethyl benzoylacetate in water in the presence of potassium hydroxide to obtain benzoylacetic acid, carrying out a condensation reaction with glutaraldehyde and methylamine hydrochloride in a citric acid buffer solution, carrying out a reduction reaction on lobeline diketone hydrochloride obtained by the condensation reaction in a mixed solution composed of potassium borohydride, activated carbon, sodium hydroxide and methanol, quenching the reducing agent in the obtained reaction liquid by sulfuric acid, sequentially filtering, extracting, concentrating, cooling and crystallizing to obtain lobeline racemate, then adding L-DBTA, and sequentially performing resolution, dissociation and hydrochlorination to obtain lobeline hydrochloride. The synthesis method has the characteristics of few synthesis steps, simple synthesis conditions, convenience in operation and the like, and the used raw materials have the characteristics of wide source, low price and the like.
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- Pd-catalyzed enantioselective aerobic oxidation of secondary alcohols: Applications to the total synthesis of alkaloids
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Enantioselective syntheses of the alkaloids (-)-aurantioclavine, (+)-amurensinine, (-)-lobeline, and (-)- and (+)-sedamine are described. The syntheses demonstrate the effectiveness of the Pd-catalyzed asymmetric oxidation of secondary alcohols in diverse contexts and the ability of this methodology to set the absolute configuration of multiple stereocenters in a single operation. The utility of an aryne C-C insertion reaction in accessing complex polycyclic frameworks is also described.
- Krishnan, Shyam,Bagdanoff, Jeffrey T.,Ebner, David C.,Ramtohul, Yeeman K.,Tambar, Uttam K.,Stoltz, Brian M.
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supporting information; experimental part
p. 13745 - 13754
(2009/02/06)
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- Enantioselective synthesis of lobeline via nonenzymatic desymmetrization
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Lobeline has been prepared in enantiopure form via desymmetrization of lobelanidine with use of BTM, a nonenzymatic enantioselective acyl transfer catalyst.
- Birman, Vladimir B.,Jiang, Hui,Li, Ximin
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p. 3237 - 3240
(2008/02/11)
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