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Synthesis method of stemona alkaloid

A synthetic method and technology of alkaloids, applied in organic chemistry methods, organic chemistry, etc., can solve problems such as low natural content, complex structure, and no total synthesis report

Active Publication Date: 2018-11-23
SHANXI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

In 2016, Professor Zhao Yongxing isolated the natural product parvistemonine from the leaves of the leaves. Due to its complex structure, there is no total synthesis report so far.
Due to the low natural content of these compounds, the systematic research and wide application of their biological activities are limited.

Method used

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  • Synthesis method of stemona alkaloid
  • Synthesis method of stemona alkaloid
  • Synthesis method of stemona alkaloid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0054] Example 1 Preparation of 4-(1H-pyrrolyl) ethyl butyrate (6)

[0055] 2,5-Dimethoxytetrahydrofuran (8.5 g, 63 mmol) was added into water (180 mL), stirred and refluxed under argon for 2 hours. The mixture was cooled to room temperature, and dichloromethane (100 mL), sodium acetate (13 g, 155 mmol) and ethyl 4-aminobutyrate hydrochloride (13 g, 78 mmol) were added, and the mixture was stirred vigorously in the dark for 15 hours. A 2M sodium carbonate solution (20 mL) was added and extracted with dichloromethane. After drying with magnesium sulfate and filtering, the filtrate was concentrated and the resulting residue was subjected to column chromatography (petroleum ether: ethyl acetate = 1:1) to obtain 9.0 g of pyrrole derivatives (yield: 77%).

[0056] FTIR (neat, cm -1 )ν max 2980, 1732, 1500, 1447, 1375, 1282, 725;

[0057] 1H NMR (500MHz, CDCl 3 )δ: 6.64(t, J=2.0Hz, 2H), 6.14(t, J=2.1Hz, 2H), 4.13(q, J=7.1Hz, 2H), 3.94(t, J=6.9Hz, 2H) ,2.27(t,J=7.3Hz,2H),2.13–...

Embodiment 2

[0060] Example 2 Preparation of N-methoxy-N-methyl-4-(1H-pyrrol-1-yl)butanamide (7)

[0061] At -20°C, a 2.0M concentration of i-PrMgCl (0.64mL, 1.27mmol) in tetrahydrofuran was added dropwise to ethyl 4-(1H-pyrrolyl)butyrate (6) (0.1g, 0.55mmol) and Me(MeO)NH·HCl (64 mg, 0.66 mmol) in anhydrous THF (1.5 mL). The mixture was slowly warmed to 0°C, stirred at 0°C for 2 hours, then quenched with saturated ammonium chloride solution. The mixture was extracted with EA. The organic layers were combined, dried over anhydrous magnesium sulfate, filtered, the filtrate was concentrated and the residue obtained was subjected to column chromatography (n-hexane:ethyl acetate=1:1) to obtain N-methoxy-N-methyl-4-(1H -Pyrrol-1-yl)butyramide 0.1 g (yield: 92%).

[0062] FTIR (neat, cm -1 )ν max 29377, 1660, 1500, 1445, 1386, 1281, 726;

[0063] 1 H NMR (500MHz, CDCl 3 )δ: 6.65(t, J=2.1Hz, 2H), 6.13(t, J=2.1Hz, 2H), 3.97(t, J=6.8Hz, 2H), 3.60(s, 3H), 3.17(s, 3H), 2.36(t, J=7.1Hz, 2H),...

Embodiment 3

[0066] Example 3 Preparation of 6-(1H-pyrrol-1-yl)hexyl-1-en-3-one (8)

[0067] To a solution of N-methoxy-N-methyl-4-(1H-pyrrol-1-yl)butanamide (2.6 g, 13.3 mmol) in THF (120 mL) gradually over 20 minutes at -20°C Vinylmagnesium chloride (1M solution in tetrahydrofuran, 16ml, 16mmol) was added dropwise, and the reaction mixture was stirred at this temperature for 2 hours. Under argon, it was quenched with water (50 mL) at -10 °C. The aqueous layer was extracted with ether, the combined organic layers were washed with saturated sodium chloride solution, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain a crude product, which was directly used in the next reaction.

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Abstract

The invention discloses a synthesis method of stemona alkaloid and belongs to the technical field of chemical synthesis. The method is characterized by comprising the following steps: at 10 DEG C below zero to 0 DEG C, adding boron trifluoride diethyl etherate (molar equivalent ratio is 3 to 1) into a dichloroethane solution of (R,E)-methyl-4-hydroxy-7-(1H-pyrrole-1-yl) heptyl-2-polymethylmethacrylate, raising the temperature of a reaction mixture to room temperature and stirring for 12 to 36 hours to obtain (3aR,10bR)-3a,4,5,6-tetrahydro-1H-furan[3,2-c]pyrrolidine[1,2-a]azepine-2(10bH)-one. The invention provides a synthesis strategy for efficiently synthesizing the stemona alkaloid parvistemonine and lays a foundation for further pharmacological activity and chemical biology research ofa natural product.

Description

technical field [0001] The invention relates to a method for synthesizing parvistemonine, a natural product, in particular to a method for synthesizing parvistemonine, which belongs to the technical field of organic synthesis. Background technique [0002] Alkaloids are an important class of natural organic compounds with complex structures and various types, and often have obvious physiological activities. For thousands of years, alkaloids have played a prominent role as medicines in the treatment and prevention of diseases. At the same time, alkaloids also play an important role in plant protection. Liliaceae plants belong to the monocot class Liliaceae subclass Pandanus, which includes 4 genera of about 25 to 35 species of plants, mostly perennial herbaceous plants with tuberous roots or tuberous stems. Centipede plants are widely distributed in East Asia, Southeast Asia and northern Australia. Various plants of the family Centipede are important medicines, which are r...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D491/147
CPCC07B2200/07C07D491/147
Inventor 马开庆任虎斌吴晓晓张丽增秦雪梅
Owner SHANXI UNIV
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