Method for enantioselective synthesis of iboga alkaloids
An enantioselective, alkaloid technology, applied in organic chemistry methods, organic chemistry, etc., can solve problems such as difficulty in providing enough samples for biological activity testing, single achiral natural product, and high cost
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Embodiment 1
[0049] Synthesis of Compound 2
[0050]
[0051] CH in compound 1 (4.9g, 21.7mmol) 2 Cl 2 (108 mL) was added successively at room temperature with di-tert-butyl dicarbonate (12 mL, 52 mmol), followed by triethylamine (3.6 mL, 26.0 mmol) and DMAP (1.1 g, 8.7 mmol). Stir at room temperature for 14h. Then the reaction mixture was distilled with CH 2 Cl 2 Dilute to saturate NH 4 Cl solution (50 mL) was quenched with CH 2 Cl 2 (3 x 50 mL) extraction. After the organic phases were combined, they were washed with saturated NaCl solution (100 mL) and washed with anhydrous NaCl 2 SO 4 dry. The solvent was removed by a rotary evaporator, and the residue was purified by silica gel column chromatography (petroleum ether:ethyl acetate=2:1). Compound 2 (6.3 g, yield 89%) was obtained as a pale yellow viscous liquid.
[0052] The detection data of compound 2 are as follows:
[0053] R f =0.40 (Silica gel, ethyl acetate)
[0054] [α]20D=+317 (c=1.3in CHCl 3 )
[0055] IR(n...
Embodiment 2
[0123] Synthesis of compound 7
[0124]
[0125] Add anhydrous cerium trichloride (60mg, 0.24mmol) in a 10mL round bottom flask. The flask was heated to 150 °C and stirred under vacuum for 3 h. The flask was filled with N 2 , cooled to 0° C., added THF (0.4 mL), and stirred for 1 h. Ethylmagnesium bromide (0.9M THF solution, 0.17mL, 0.15mmol) was added at 0°C, stirred for 1h, then a THF (0.4mL) solution of compound 6 (20mg, 0.07mmol) was added at 0°C, stirred for 30min. Use saturated NH 4 Cl solution (1 mL) was quenched with CH 2 Cl 2 (3 x 5 mL) extraction. After combining the organic layers, use Na 2 SO 4 dry. The solvent was removed using a rotary evaporator, and the residue was purified using silica gel column chromatography (dichloromethane:methanol=100:1 to 50:1). Compound 7 (15.9 mg, yield 72%) was obtained.
[0126] The detection data of compound 7 are as follows:
[0127] R f =0.34 (dichloromethane / methanol=20:1)
[0128] [α] 20D = +29 (c = 1.0in MeOH)...
Embodiment 3
[0154] Synthesis of compounds 10 and 9
[0155]
[0156] To a solution of compound 8 (100 mg, 0.36 mmol) in ethanol (3.5 mL) was added Fe(acac) at room temperature 3 (101.3 mg, 0.29 mmol) and phenylsilane (110 μL, 0.89 mmol). Use a vacuum pump to remove the gas in the flask, and then fill it with N 2 , repeated several times, and added tert-butanol peroxide (5.0M-6.0M decane solution, 98 μL, 0.54 mmol). Use a vacuum pump to remove the gas in the flask, and then fill it with N 2 , repeated several times. Warm up to 60°C and stir for 6h. The reaction mixture was CH 2 Cl 2 Diluted, quenched with water (3 mL), washed with 10% methanol in CH 2 Cl 2 (3 x 5 mL) extraction. After combining the organic layers, use Na 2 SO 4 dry. The solvent was removed by a rotary evaporator, and the residue was purified by silica gel column chromatography (dichloromethane to dichloromethane:methanol=20:1) to obtain a mixture of compounds 10 and 9. The mixture was separated using PTLC (...
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