Synthesis method and application of natural alkaloid arbornamine with anti-inflammatory activity
A synthesis method and technology of alkaloids, applied in anti-inflammatory agents, drug combinations, organic chemistry, etc., can solve the problems of high cost of separation and purification process, obstacles to rapid development and application of drugs, scarcity of total natural products, etc. Good compatibility and mild conditions
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Embodiment 1
[0089] The preparation process of natural alkaloid Arbornamine is as follows:
[0090] (1) Preparation of compound diester 2:
[0091] A 250mL round bottom flask was added with a stirring bar, 1 (8.5 g, 29.7 mmol) was added, absolute ethanol (100 mL), diethyl ketomalonate (6.3 mL, 41.6 mmol) were added, and the reaction was carried out at 100 o After stirring at C for 6 days, return to room temperature, remove ethanol by rotary evaporation, add ethyl acetate (50 mL) to dilute, then add saturated sodium bicarbonate solution to adjust the pH of the aqueous phase to about 9, extract three times with ethyl acetate, and combine the organic phases Backwash with saturated sodium chloride solution, dry over anhydrous sodium sulfate, filter and concentrate. The concentrate was purified by silica gel column chromatography (petroleum ether / ethyl acetate=6 / 1) to obtain compound 2 (yellow solid, 9.6 g, 80%). 1 H NMR (400 MHz, CDCl 3 ) δ 8.33 (s, 1H), 7.51 (t, J = 8.7 Hz, 3H), 7.33 (t,...
Embodiment 2
[0107] Preparation of Compound 5:
[0108] A 100 mL round bottom flask was added with a stir bar, added 4 (1.0681 g, 2.5 mmol), added ethyl acetate (25 mL), replaced nitrogen 3 times, and then added Pd(OH) 2 / C (10%, 351.9 mg, 0.25 mmol), after replacing the hydrogen gas (balloon) 3 times, react overnight at room temperature under hydrogen atmosphere, filter the palladium carbon with diatomaceous earth, collect the filtrate, and concentrate. The concentrate was purified by silica gel column chromatography (dichloromethane / methanol=30 / 1) to obtain compound 5 (white solid, 656 mg, 78%).
Embodiment 3
[0110] Preparation of Compound 6:
[0111] Add 5 (890 mg, 2.65 mmol) to the 4 mL reaction flask, add 5 (890 mg, 2.65 mmol), add potassium carbonate (1.46 g, 10.6 mmol), activated 4 Å molecular sieves, ultra-dry acetonitrile (5.3 mL), and dropwise add (Z)- 1-Bromo-2-iodo-2-butene (0.62 mL, 4.77 mmol), reacted at 70 o Stir overnight at C, dilute with water, extract three times with ethyl acetate, combine the organic phases and backwash with saturated sodium chloride solution, dry over anhydrous sodium sulfate, filter, and concentrate. The concentrate was purified by silica gel column chromatography (petroleum ether / ethyl acetate=10 / 1) to obtain compound 6 (yellow solid, 1.28 g, 93%).
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