Method for synthesizing natural product (+/-)-folicanthine and intermediate product thereof

A synthetic method and technology of natural products, applied in the field of medicine, can solve problems such as difficulties in industrial production, high reaction temperature, and many reaction steps, and achieve the effects of high yield, low reaction temperature, and few reaction steps

Inactive Publication Date: 2014-07-23
LANZHOU UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In recent years, there are many studies on the synthesis of hexahydropyrrolidindole, but a large amount of metals are used, which causes pollution to the environment; many reaction steps, low yield, relatively high reaction temperature and other factors bring certain difficulties to industrial production

Method used

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  • Method for synthesizing natural product (+/-)-folicanthine and intermediate product thereof
  • Method for synthesizing natural product (+/-)-folicanthine and intermediate product thereof
  • Method for synthesizing natural product (+/-)-folicanthine and intermediate product thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] A kind of synthetic method of the intermediate product of natural product (±)-folicanthine, described method is:

[0040] At 25°C, mix 10 mmoles of compound a with 20 mmoles of Cs 2 CO 3 Dissolve in 50 ml of acetonitrile, add 20 mmoles of iodine and stir at 25°C for 30 min; then add saturated Na 2 S 2 o 3 Quench the reaction and continue to add saturated Na 2 S 2 o 3 Shake continuously until the iodine is removed, and extract 3 times with ethyl acetate, each with 100 ml. The combined organic phases were washed with anhydrous Na 2 SO 4 Dry, spin out the solvent, wash and separate on a silica gel column with mobile phase petroleum ether: ethyl acetate = 8:1, the obtained compound b is 8,8'-dimethyl-1,1'-di-p-toluenesulfonate Acyl-2,2′,3,3′,8,8a,8′,8′a-octahydro-1H,1′H-3a,3′a-dipyrrole[2,3-b]indole White solid, 90% yield.

[0041] Characterization data of compound b: white solid Mp: 149-152°C; 1H NMR (400MHz, CDCl 3 , TMS) δ7.36(d, J=8.0Hz, 4H), 7.21-7.27(m, 6H...

Embodiment 2

[0051] A kind of synthetic method of the intermediate product of natural product (±)-folicanthine, described method is:

[0052] At room temperature, 5 mmoles of compound a and 10 mmoles of Cs 2 CO 3 Dissolve in 25 ml of acetonitrile, add 10 mmol of iodine and stir at room temperature for 10 minutes; then add saturated Na 2 S 2 o 3 Quench the reaction and continue to add saturated Na 2 S 2 o 3 Shake continuously until the iodine is removed, and extract 3 times with ethyl acetate, each dosage is 50 ml. The combined organic phases were washed with anhydrous Na 2 SO 4 Dry, spin out the solvent, wash and separate on the silica gel column with mobile phase petroleum ether: ethyl acetate = 8:1, the obtained compound b is 8,8'-dimethyl-1,1'-di-p-toluenesulfonate Acyl-2,2′,3,3′,8,8a,8′,8′a-octahydro-1H,1′H-3a,3′a-dipyrrole[2,3-b]indole White solid, 91% yield.

[0053] The synthetic method of preparing natural product (±)-folicanthine with compound b as an intermediate produ...

Embodiment 3

[0059] A kind of synthetic method of the intermediate product of natural product (±)-folicanthine, described method is:

[0060] At room temperature, 2 mmoles of compound a and 4 mmoles of Cs 2 CO 3 Dissolve in 10 ml of acetonitrile, add 4 mmol of iodine and stir at room temperature for 20 minutes; then add saturated Na 2 S 2 o 3 Quench the reaction and continue to add saturated Na 2 S 2 o 3 Shake continuously until the iodine is removed, and extract 3 times with ethyl acetate, each dosage is 20 ml. The combined organic phases were washed with anhydrous Na 2 SO 4 Dry, spin out the solvent, wash and separate on a silica gel column with mobile phase petroleum ether: ethyl acetate = 8:1, the obtained compound b is 8,8'-dimethyl-1,1'-di-p-toluenesulfonate Acyl-2,2′,3,3′,8,8a,8′,8′a-octahydro-1H,1′H-3a,3′a-dipyrrole[2,3-b]indole White solid, 92% yield.

[0061] The synthetic method of preparing natural product (±)-folicanthine with compound b as an intermediate product i...

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PUM

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Abstract

The invention discloses a method for synthesizing a natural product (+ / -)-folicanthine and an intermediate product thereof, belonging to the field of medicine. The method for synthesizing the intermediate product comprises the steps of: dissolving 4-methyl-N-(2-(1-methyl-1H-indole-3-)ethyl) p-toluenesulfonamide and Cs2CO3 in a solvent; adding a catalyst; and stirring to obtain the intermediate product. The method for synthesizing the natural product comprises the steps of: preparing the intermediate product; adding sodium in tetrahydrofuran to generate a sodium-naphthalene solution; adding the sodium-naphthalene solution into a tetrahydrofuran solution of the intermediate product to prepare a compound c; and adding sodium triacetoxyborohydride and formalin into an acetonitrile solution of the compound c, stirring, dropwise-adding an ammonia-saturated mixed solution of methanol and methylene dichloride, and concentrating and purifying a reactant to obtain the natural product. The method disclosed by the invention has the advantages of less reaction steps, environment friendliness in reaction, no use of metallic catalyst, high yield rate, moderate reaction conditions, no need of further treatment of the solvent and less pollution to the environment.

Description

technical field [0001] The invention relates to a synthetic method of a natural product (±)-yekansheng and an intermediate product thereof, belonging to the technical field of medicine. Background technique [0002] In recent years, some reactions of indole derivatives and their synthesis have been the research hotspots in the field of organic chemistry. Since many drugs and biologically active natural products are derived from the skeleton of indole, it has become an important frontier of organic chemistry. research direction. The chemical formula of hexahydropyrrolidindole is C 24 h 30 N 4 , is a natural product with a unique structure, and more natural products can be derived from its skeleton. [0003] The reason why the structures of these alkaloids are so fascinating in recent years is that their biological activities have aroused great interest in the total synthesis of these natural products. The general promotion method of these natural products is the intramole...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D487/04
Inventor 梁永民李英秀王海锡
Owner LANZHOU UNIVERSITY
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