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Total synthesis method of mangostin

A synthesis method and compound technology, applied in the field of synthesis of natural product mangostin, can solve the problems of long cycle, harsh reaction conditions, limited sources, etc.

Active Publication Date: 2012-09-05
CHINA PHARM UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0018] Mainly there are following shortcomings in the above-mentioned synthesis method: 1. method one and method two are all synthesized by segmented method, and reaction step is long, and yield is extremely low, and reaction condition is harsh, and most of reaction cost is too high, is difficult to adapt to large-scale production; ②The third method is to use the separated natural products for semi-synthesis, but the existing separation methods are cumbersome, the cycle is very long, and the yield is extremely low, so the source is very limited

Method used

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  • Total synthesis method of mangostin
  • Total synthesis method of mangostin
  • Total synthesis method of mangostin

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0067] The preparation of 2,4,5-trimethoxybenzoyl chloride (V):

[0068] Dissolve 4.24g (0.02mol) of 2,4,5-trimethoxybenzoic acid in 50mL of dichloromethane, add 6mL of oxalyl chloride, stir at room temperature, evaporate the solvent under reduced pressure, and directly put it into the next reaction.

Embodiment 2

[0070] 2-Hydroxy-2',4,4',5',6-pentamethoxybenzophenone (VIb) and 2-Hydroxy-2',4,4',5',6-pentamethoxy Preparation of benzophenone (VIa):

[0071] Add 60 mL of diethyl ether to the solid 2,4,5-trimethoxybenzoyl chloride (V) prepared in Example 1, slowly add 3.30 g (0.018 mol) of 1,3,5-trimethoxybenzene, batch by batch 9.35 g (0.07 mol) of aluminum trichloride was added, and the reaction solution turned blood red, and massive viscous solids appeared. The ice bath was removed and refluxed for 36 hours. Extracted with ethyl acetate and purified by silica gel column chromatography (petroleum ether / ethyl acetate=4:1) to obtain 2-hydroxy-2',4,4',5,6'-pentamethoxy as a yellow granular solid Benzophenone (VIa) 1.3g, yield 20%, compound 2-hydroxy-2',4,4',5',6-pentamethoxybenzophenone (VIb) 1.5g, yield 22 %.

[0072] Compound VIa

[0073] 1 H-NMR (300MHz, CDCl 3 ): δ3.72(s, 6H, C 4 -OCH 3 , C 5 -OCH 3 ), δ3.86(s, 3H, C 4’ -OCH 3 ), δ3.88(s, 6H, C 2’ -OCH 3 , C 6’ -OCH 3 )...

Embodiment 3

[0079]Preparation of 1,3,6,7-tetramethoxyxanthone (VII):

[0080] 2-Hydroxy-2',4,4',5,6'-pentamethoxybenzophenone (VIa) or 2-hydroxy-2',4,4',5',6-pentamethoxy A total of 3.48g (0.01mol) of benzophenone (VIb) was dissolved in 60mL of methanol, 90mL of water and 6.0g (0.15mol) of sodium hydroxide were added, refluxed at 80°C for 24 hours, cooled to room temperature, a large number of light yellow flocs appeared After suction filtration and drying, methanol was recrystallized to obtain 2.76 g of off-white amorphous solid 1,3,6,7-tetramethoxyxanthone (VII), with a yield of 87.3%.

[0081] 1 H-NMR (300MHz, CDCl 3 ): δ3.90(s, 3H, C 3 -OCH 3 ), δ3.97(s, 6H, C 6 -OCH 3 , C 7 -OCH 3 ), δ3.98(s, 3H, C 1 -OCH 3 ), δ6.34(s, 1H, C 4 -H), δ6.46(s, 1H, C 5 -H), δ6.81(s, 1H, C 2 -H), δ7.65(s, 1H, C 8 -H);

[0082] EI-MS (m / z): 316 (M + ), 299, 287, 270, 185, 83.

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Abstract

The invention belongs to the field of chemical synthesis, in particular relates to a synthesis method of a natural product mangostin which is shown in the formula (I) and has good anti-tumor activity, anti-inflammation activity and anti-bacterial activity. The method provided by the invention comprises the following steps of: taking 2,4,5-trialkoxy benzoic acid and 1,3,5-trialkoxy benzene as initial raw materials; carrying out acyl chlorination, Friedel-Crafts acylation and cyclization to prepare a key intermediate 1,3,6,7-tetraalkoxy xanthone; and then, carrying out dealkylation, allylation, Claisen rearrangement, methylation, oxidation reaction, WITTING reaction and dealkylation reaction so as to prepare the mangostin.

Description

technical field [0001] The invention belongs to the field of chemical synthesis, and in particular relates to a method for synthesizing the natural product mangostin represented by formula (I) with good antitumor activity, anti-inflammatory and antibacterial activities. [0002] Background technique [0003] Mangosteen (Garcinia mangostana L) is a plant widely distributed in tropical regions of Southeast Asia. Its peel and bark have been used by local residents as traditional Chinese medicine for many years to treat fever, dysentery, wound infection and other diseases, and its fruit It has rich nutritional value and is known as the king of fruits (Phytochemistry. 1997, 44: 191-214; J Agric Food Chem. 2007, 55: 7689-94; J Agric Food Chem. 2002, 50: 7449-7454). Natural medicinal chemistry research has found that a series of secondary metabolites contained in the mangosteen plant, such as xanthone compounds containing oxygen-containing rings and isopentenyls, have been prove...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/86C07F9/535
Inventor 王进欣叶红春王帆尤启冬顾勤兰
Owner CHINA PHARM UNIV
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