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Anti-trypanosome anticancer natural product Cryptofolione synthesizing method

A technology of natural products and synthetic methods, applied in the production of bulk chemicals, organic chemistry, etc., can solve the problems of long routes and expensive synthesis costs, and achieve the effects of good reaction selectivity, simple operation, and fewer linear steps

Active Publication Date: 2018-09-04
DONGGUAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] The purpose of the present invention is to overcome the problems of long routes and expensive synthesis costs in the existing synthetic methods, and provides a new synthetic method of the natural product Cryptofolione

Method used

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  • Anti-trypanosome anticancer natural product Cryptofolione synthesizing method
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  • Anti-trypanosome anticancer natural product Cryptofolione synthesizing method

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Embodiment 1

[0025] 1. Synthesis of the compound of formula 3: Weigh (R)-BINOL (0.14g, 0.48mmol) and (1.06g) was added to anhydrous tetrahydrofuran (1mL), and then Ti(O i Pr) 4 (70 μL, 0.24 mmol), and the resulting mixture was stirred at room temperature for 1 hour, and then the mixture was cooled to -78°C. A solution of acrolein (0.64 g, 3.03 mmol) in tetrahydrofuran was added dropwise. After reacting for 30 minutes, the compound of dienosilyl ether formula 2 (2.37 g, 9.09 mmol) was dissolved in tetrahydrofuran and introduced with a double-ended catheter. The resulting solution was stirred at -78°C under nitrogen for 2 hours, then transferred to room temperature and stirred overnight. After the reaction of acrolein was complete, the mixture was re-cooled to -78°C and trifluoroacetic acid (1.21 mL) was added dropwise. Warm to room temperature and continue stirring for 1 hour. It was then diluted with a small amount of ethyl acetate (5 mL), and saturated aqueous sodium bicarbonate (5 ...

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Abstract

The invention discloses an anti-trypanosome anticancer natural product Cryptofolione synthesizing method. The synthesizing method disclosed by the invention comprises the steps: after acrolein and silyl enol ether are utilized to perform Mukaiyama aldol reaction, sodium borohydride is used for reducing ketone into alcohol, and then pyridinium p-toluenesulfonate refluxes in a methylbenzene solutionto obtain compound shown in a formula 5; after cinnamyl aldehyde and an evans chiral aid are used for performing evans aldol reaction, diisobutyl aluminum hydride is used for reducing the cinnamyl aldehyde and the evans chiral aid at first, and then addition with metal indium activated 3-propylene bromine is performed to obtain compound shown in a formula 9; the compound shown in the formula 9 isresolved and purified for many times by kinetic resolution; the compound shown in the formula 9 and 2,2-diemthoxy propane can obtain fragment type 10 compound under the pyridinium p-toluenesulfonatecondition, the fragment type 10 compound and fragment type 5 compound can generate olefin metathesis reaction through a Grubbs secondary catalyst, and protecting groups of the fragment type 10 compound are removed under the hydrochloric acid condition to obtain Cryptofolione.

Description

technical field [0001] The invention relates to a synthesis method of Cryptofolione, an anti-trypanosome and anti-cancer natural product, specifically belonging to the field of organic synthesis. Background technique [0002] Trypanosomes are parasitic organisms. Among protozoa, trypanosomes are characteristically capable of penetrating tissues in another organism, feed primarily on blood, and are also somewhat harmful to lymph. This behavior can cause many diseases, such as trypanosomiasis in humans (Chagas disease in South America), pernicious anemia (surra), and brucellosis-like disease in cattle, all tropical diseases, mainly in Fifteen tropical countries in Africa and South America. On November 10, 2014, the American Society of Tropical Medicine and Hygiene warned that Chagas Disease is raging in the United States, and it is estimated that more than 300,000 people have been infected. Pharmacological experiments of Cryptofolione show that it has significant anti-trypa...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D309/32
CPCC07D309/32Y02P20/55
Inventor 王晓季李旺王博肖和盛周毅王继武庞易英彭莹孙永丽黄双平
Owner DONGGUAN UNIV OF TECH
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