Method for fully synthesizing natural product cerbinal and application ofcerbinal

A natural product, total synthesis technology, applied in the field of pesticides, can solve problems such as mass preparation of unfavorable natural products, research on unfavorable biological activity, easy deterioration, etc., and achieve the effects of easy industrial amplifying synthesis, shortening the synthesis route, and improving the total yield.

Active Publication Date: 2019-10-29
INST OF APPLIED CHEM JIANGXI ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This process requires protection and deprotection of functional groups, and the 1,1’-thiocarbonyldiimidazole used in the process is expensive and easy to deteriorate
It is not conducive to the large-scale preparation of natural products, and it is also not conducive to the study of subsequent biological activities

Method used

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  • Method for fully synthesizing natural product cerbinal and application ofcerbinal
  • Method for fully synthesizing natural product cerbinal and application ofcerbinal
  • Method for fully synthesizing natural product cerbinal and application ofcerbinal

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] Total synthetic route of mangolin:

[0021]

[0022] Concrete preparation steps are as follows:

[0023] 8.00 g (35.4 mmol) of genipin, 10.89 g (38.9 mmol) of 2-iodobenzoic acid (IBX) and 200 ml of dimethyl sulfoxide were added to a 500 mL round bottom flask. Under argon protection, after electromagnetic stirring at room temperature for 3 h, 300 mL of water was added. Suction filtration, the filtrate was extracted four times with ethyl acetate, the organic phases were combined, washed with water, washed with saturated brine, dried over anhydrous magnesium sulfate, suction filtered, and precipitated to obtain the crude product of 1, and the pure product of compound 1 was obtained by column chromatography. It is light yellow solid.

[0024] In 250mL round bottom flask, add compound 1 (1.00g, 4.46mmol), DDQ (1.01g, 4.46mmol), CF 3 SO 3 H (0.67g, 4.46mmol), 100mL dichloromethane. Stir at room temperature, TLC tracking reaction complete, after cooling, add sodium car...

Embodiment 2

[0026] The second step of the total synthetic route of mangolin can also be carried out by the following method:

[0027]

[0028] Compound 1 (1.00 g, 4.46 mmol), DDQ (1.06 g, 4.68 mmol), TsOH (0.77 g, 4.46 mmol), and 100 mL of toluene were added to a 250 mL round bottom flask. Heat and stir at 100°C, after TLC traces the complete reaction, add aqueous sodium carbonate solution after cooling, separate liquids, wash the aqueous phase twice with ethyl acetate, combine the organic phases, wash once with water, wash once with saturated sodium chloride, anhydrous magnesium sulfate Drying, suction filtration, precipitation, and column chromatography yielded the natural product marmandal, which was a bright yellow solid with a yield of 76%.

Embodiment 3

[0030] The second step of the total synthetic route of mangolin can also be carried out by the following method:

[0031]

[0032] Compound 1 (1.00g, 4.46mmol), DDQ (1.32g, 5.80mmol), trifluoroacetic acid (5.09g, 44.6mmol), and 100mL 1,2-dichloroethane were added to a 250mL round bottom flask. Heat and stir at 80°C, after TLC traces the complete reaction, add aqueous sodium carbonate solution after cooling, separate the liquids, wash the aqueous phase twice with ethyl acetate, combine the organic phases, wash once with water, wash once with saturated sodium chloride, anhydrous magnesium sulfate Drying, suction filtration, precipitation, and column chromatography yielded the natural product marmandal, which was a bright yellow solid with a yield of 83%.

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Abstract

The invention relates to a method for fully synthesizing natural product cerbinal and application in plant protection, and belongs to the technical field of pesticides. The method comprise the steps that genipin is used as a raw material; the first step, the raw material genipin is oxidized by IBX to obtain a compound 1; and the second step, DDQ and acid are added, and the compound 1 is oxidized and dehydrated to obtain the cerbinal. The method does not adopt a protecting group strategy, first, IBX only oxidizes a primary hydroxyl group and does not react with an acetal hydroxyl group to obtain an intermediate 1; and then, oxidative dehydrogenation and elimination of dehydration are completed simultaneously, the natural product cerbinal is synthesized only in two steps, a synthetic route is significantly shortened, and the application prospects are good. It is found the first time that the natural product cerbinal has anti-plant virus, insecticidal and bactericidal activity by the method, and the cerbinal can be developed as a novel plant-derived pesticide or as a lead compound.

Description

technical field [0001] The invention belongs to the technical field of pesticides, and in particular relates to a synthesis method of a natural product mangolin, and also relates to its application in plant protection. Background technique [0002] As the global population continues to increase and people's dietary structure changes, the pressure on food production is also increasing. Diseases, insects, and weeds pose a great threat to food production, and need to be continuously and effectively prevented. At the same time, the environmental, toxicological and management requirements for the application of agrochemical products are becoming increasingly stringent, and the requirements for pest control products are also increasing. The continuous development of pest resistance to control agents further limits the application of drugs. Therefore, it is necessary to continuously discover and develop new, effective and economical pest control agents to increase the yield of cr...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/94A01N43/16A01P7/04A01P1/00A01P3/00
CPCC07D311/94A01N43/16Y02P20/55
Inventor 李玲邹吉勇游胜勇韩晓丹邓朝阳
Owner INST OF APPLIED CHEM JIANGXI ACAD OF SCI
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