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Asymmetric synthesis method of galanthamine and lycoramine

A technology of galantamine and synthesis method, which is applied in the field of synthesis of natural products with complex structures, can solve problems such as low cost, lack of economy, and expensive catalyst, and achieve cost saving, great novelty, and high reaction repeatability Effect

Inactive Publication Date: 2015-05-06
PEKING UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

As we all know, the catalysts for asymmetric catalysis are expensive, and the later the catalytic reaction is realized, the lower the overall cost. In the methods reported in the two patents, the asymmetric catalytic reaction is carried out in the early stage of synthesis, which is not economical.

Method used

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  • Asymmetric synthesis method of galanthamine and lycoramine
  • Asymmetric synthesis method of galanthamine and lycoramine
  • Asymmetric synthesis method of galanthamine and lycoramine

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Embodiment Construction

[0038] The following are the specific synthesis process and structural characterization data of the compounds of the present invention.

[0039] Preparation of compound 3

[0040] Compounds 1 (2.51g, 9.0mmol) and 2 (1.64g, 9.0mmol) were dissolved in 25mL of methanol, and at -10°C, NaBH was added 4 (692mg, 18.2mmol, 2.02equiv), stirred at room temperature for 1h. Add triethylamine (1.5mL, 10.8mmol, 1.20equiv) and (Boc) to the reaction solution 2 O (1.96g, 9.1mmol, 1.01equiv), stirring was continued at room temperature for 2h. The reaction solution was concentrated under reduced pressure, then 30 mL of water was added, extracted with ethyl acetate (100 mL×3), and the organic phases were combined with anhydrous Na 2 SO 4 After drying and concentrating under reduced pressure, compound 3 (4.9 g) was isolated by column chromatography (petroleum ether / ethyl acetate, 10:1).

[0041] The yield of this step is 81%, and the relevant analysis data are as follows

[0042] 1 H NMR (4...

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Abstract

The invention discloses an asymmetric synthesis method of galanthamine and lycoramine. According to the asymmetric synthesis method, the iodide of cheap and easily available raw material isovanillin and easily prepared 4-triethylsilyl-3-butyne-1-amidogen are taken as raw materials, a coumarone compound can be produced by virtue of a palladium catalytic Larock cyclization reaction after the nitrogen atom is protected by virtue of reductive amination, next, an optical pure key intermediate can be obtained at the ee value of 94% by virtue of the asymmetric michael addition of p-methyl vinyl ketone under the catalysis of critical metal Sc(OTf)3 and oxynitride ligands after the coumarone compound is transformed into a coumaranone structure, and the intermediate is subjected to the asymmetric adol reaction induced chirally by a substrate and subsequent selective reduction of lithium tri-sec-butylborohydride so that optically pure galanthamine and lycoramine can be obtained. The asymmetric synthesis method has the advantages of shorter synthesis route and higher efficiency.

Description

technical field [0001] The invention relates to the synthesis of a natural product with a complex structure, in particular to the catalyzed asymmetric synthesis of the drug galantamine and the natural product lycamine. Background technique [0002] Galantamine, the English name is Galanthamine, the chemical name is {(4aS,6R,8aS)-4a,5,9,10,11,12-hexahydro-3-3-methoxy-11-methyl- Benzofuran-[3a,3,2-ef]-[2]azepin-6-ol}, molecular formula: C 17 h 21 NO 3 . Licamine is the hydrogenated product of galantamine. Both galantamine and lycamine are natural active alkaloids isolated from Amaryllidaceae plants Snowdrop, Lycoris and related plants. [0003] The molecular structures and configurations of natural Galanthamine and Lycoramine are as follows: [0004] [0005] Pharmacological studies have shown that on the one hand, galantamine has potent reversible acetylcholinesterase (aeetylcholinesterase, AChE) inhibitory activity, and on the other hand has the conformational regul...

Claims

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Application Information

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IPC IPC(8): C07D491/107
CPCY02P20/55C07D491/107C07B53/00
Inventor 贾彦兴杨巧李磊
Owner PEKING UNIV
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