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Method for synthesizing highly active macrolide Ivorenolide B

A macrolide, synthesis method technology, applied in the directions of organic chemistry, organic chemistry, etc., can solve the problems such as complicated steps, the problem of macrolide cis-trans can not be solved well, and achieves simple operation and synthesis. Low cost and the effect of eliminating side reactions

Active Publication Date: 2018-08-24
HENAN AGRICULTURAL UNIVERSITY
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Problems solved by technology

[0003] There are few known methods for synthesizing the macrolide Ivorenolide B, and the steps are generally cumbersome (Organic Letters, 2014, 16(7): 2062-2065.)
For example, the method reported by Wang has a total of 7 steps from the substrate to the product synthesis, and the cis-trans problem of macrolides has not been well resolved.

Method used

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  • Method for synthesizing highly active macrolide Ivorenolide B
  • Method for synthesizing highly active macrolide Ivorenolide B

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Embodiment

[0028] The synthetic method of the highly active macrolide Ivorenolide B of the present embodiment, the structure of the highly active macrolide Ivorenolide B is The synthetic method of described macrocyclic lactone Ivorenolide B comprises the following steps:

[0029] (1) Synthesis of chiral alcohol esters: In a Shrek tube equipped with a magnetic stirrer, (S)-1-bromo-1-pentyn-3-ol (1.6301g, 10mmol), 9-decane Dienoic acid (1.7025g, 10mmol), dichloromethane 100ml, dicyclohexylcarbodiimide (4.1236g, 20mmol), 4-dimethylaminopyridine (12.3mg, 0.1mmol), after the system was clarified, refluxed for 16h, The progress of the reaction was monitored at any time by thin-layer chromatography. After the reaction was completed, the reaction solution was suction-filtered sequentially, the filter cake was washed with dichloromethane, the combined organic layer was washed with water, washed with sodium chloride, dried over anhydrous sodium sulfate, desolvated and purified by column chromato...

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Abstract

The invention discloses a method for synthesizing highly active macrolide Ivorenolide B. The structure of the highly active macrolide Ivorenolide B is as shown in the specification. The method for synthesizing the highly active macrolide Ivorenolide B is as follows: (S)-1-Bromo-1-pentyne-3-ol is used as a starting material for reacting at a reasonable ratio to synthesize an important intermediatecompound chiral alcohol ester, and the highly active macrolide Ivorenolide B is synthesized by coupling reaction, ring closure reaction, desiliconization and epoxidation reaction. The method for synthesizing the highly active macrolide Ivorenolide B is simple in synthesis route, simple and easy in raw materials, low in synthesis cost, mild in reaction conditions, and simple in separation and purification operation, a high purity target compound can be directly obtained, and the high purity target compound has high yield and optical purity, low cost, and commercial Value.

Description

technical field [0001] The invention relates to the technical field of chemical synthesis, in particular to a method for synthesizing a highly active macrolide Ivorenolide B. Background technique [0002] Khaya ivorensis, also known as African mahogany or Lagos mahogany, grows mainly in the lowland tropics and is now found mainly in Angola, Cameroon, Côte d'Ivoire, Gabon, Ghana, Liberia and Nigeria. The tree's bark is bitter, and concoctions of it are often used by locals as a natural remedy for ailments such as whooping cough, diarrhea, and dysentery. Because of this special activity, the active substances extracted from neem kaya have been widely concerned by the pharmaceutical community. Ivorenolide B, a macrocyclic lactone, is a kind of substance with high activity extracted from neem. Modern drug activity studies have proved that Ivorenolide B and its optical isomers have good immunosuppressive activity. Therefore, it is particularly important in the development of i...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D493/04
CPCC07B2200/07C07D493/04
Inventor 刘佳那日松李洪连丁胜利张猛陈琳琳周琳冯献礼游秀峰孙淑君王长青刘炳杉
Owner HENAN AGRICULTURAL UNIVERSITY
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