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A Total Synthesis Method of Natural Product Isoherinone J
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Hericium erinone, total synthesis technology, applied in the direction of organic chemistry and the like, can solve the problems of complex structure, limited application of isobenzofuranone compounds, less research on total synthesis, etc., and achieves high reaction yield and easy availability of raw materials. , the effect of simple raw materials
Inactive Publication Date: 2021-04-16
MARINE BIOMEDICAL RES INST OF QINGDAO CO LTD
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Problems solved by technology
[0006] However, due to the relatively complex structure, there are few studies on total synthesis, which limits the further application of this class of isobenzofuranones in drug development.
Method used
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Embodiment 1
[0046] 1) Synthesis of 3-hydroxyl-4-iodo-5-methoxybenzoic acid methyl ester 2, the specific process is as follows:
[0047] 29.4g (0.1mol, 99%) of methyl 3,5-dihydroxy-4-iodobenzoate, 27.6g of potassium carbonate (0.2mol, 98%, 2eq) and 200g of DMF were successively added into a dry 1L four-necked flask, Slowly add 17.03g of iodomethane (0.12mol, 99%, 1.2eq.) dropwise at room temperature. After the dropwise addition, stir and react at room temperature for 24h, TLC detection, the reaction raw material is 3,5-dihydroxy-4-iodobenzoic acid methyl ester Complete conversion.
[0048] After the reaction is completed, cool down to room temperature, add 500g of saturated ammonium chloride solution to quench the reaction, stir for 0.5h, add ethyl acetate for extraction and stratification, and keep the organic phase; wash the organic phase twice with 2*250g water; add anhydrous sulfuric acid to the organic phase Sodium drying, filtration, and concentration; a light yellow viscous liquid ...
Embodiment 2
[0070] 1) Synthesis of 3-hydroxyl-4-iodo-5-methoxybenzoic acid methyl ester 2, the specific process is as follows:
[0071] 29.4g (0.1mol, 99%) of methyl 3,5-dihydroxy-4-iodobenzoate, 27.6g of potassium carbonate (0.2mol, 98%, 2eq) and 200g of DMF were successively added into a dry 1L four-necked flask, Slowly add 17.03g of methyl iodide (0.12mol, 99%, 1.2eq) dropwise at room temperature. After the dropwise addition, stir the reaction at room temperature for 24 hours. TLC detection shows that the reaction raw material 3,5-dihydroxy-4-iodobenzoic acid methyl ester is transformed into completely.
[0072] After the reaction is completed, cool down to room temperature, add 500g of saturated ammonium chloride solution to quench the reaction, stir for 0.5h, add ethyl acetate for extraction and stratification, and keep the organic phase; wash the organic phase twice with 2*250g water; add anhydrous sulfuric acid to the organic phase Sodium drying, filtration, and concentration; a l...
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Abstract
The invention discloses a total synthesis method of isobenzofuranone natural compound J. Using methyl 3,5-dihydroxy-4-iodobenzoate as the starting material, after methylation reaction, Friedel-Crafts alkylation and transesterification, the isobenzofuranone intermediate 3 is obtained, and then the hydroxyl group is protected, It is made into tin reagent intermediate 5, and then undergoes Stille coupling reaction with geranyl acetate to generate isohericone J after deprotection. In the present invention, the raw materials are simple and easy to obtain, the reaction conditions of each unit in the reaction process are mild and controllable, and the reaction yield is high, so it has important application value in the total synthesis of natural product isohericone J and drug discovery.
Description
technical field [0001] The invention relates to a natural isobenzofuranone compound, in particular to a method for the total synthesis of isohericone J, and belongs to the technical field of natural product synthesis. Background technique [0002] Hericium erinaceus is a medicinal and edible fungus. It has a flat taste and a sweet taste. It enters the stomach meridian, helps digestion, benefits the five internal organs, strengthens the body, and has the effect of strengthening the brain and refreshing the mind. Related extracts of polysaccharides, fatty acids, diterpenoids, alkaloids, sterols, and aromatic compounds such as Isohericenone J (Isohericenone J), Hericenone A (Hericenone) are effective in the treatment of digestive tract diseases, Neurological dysfunction, diabetes, tumors and other aspects have aroused widespread concern. [0003] Iso-Hericone J is an isobenzofuranone derivative isolated from Hericium erinaceus, and its structural formula is as follows: [0...
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Patent Type & Authority Patents(China)
IPC IPC(8): C07D307/88
CPCC07D307/88
Inventor 唐宇曹伟陈平李雨田帅
Owner MARINE BIOMEDICAL RES INST OF QINGDAO CO LTD
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