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Method for synthesizing natural product Tarchonanthuslactone isomer

A technology of natural products and isomers, applied in the chemical industry, can solve the problems of slow rate, expensive reagents, and many side reactions, and achieve the effect of fast rate, easy operation, and few side reactions

Inactive Publication Date: 2015-03-11
JIANGXI SCI & TECH NORMAL UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] The purpose of the present invention is to provide a kind of preparation method of polyketone natural product Tarchonanthuslactone isomer, aiming to solve the existing research on the synthesis route of Tarchonanthuslactone isomer in the country, the existing two cases of foreign countries report the route is long, the reagent is expensive and It is highly toxic, and some reactions have problems such as slow rate, low yield, and many side reactions

Method used

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  • Method for synthesizing natural product Tarchonanthuslactone isomer
  • Method for synthesizing natural product Tarchonanthuslactone isomer

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Embodiment 1

[0034] The synthesis of embodiment 1PMB ester

[0035] Under nitrogen protection, dissolve p-methoxybenzyl alcohol (5.565g) in ether (13ml), add (403mg, 60%) NaH at 0°C, stir at room temperature for 30min, then cool to 0°C, and add dropwise Trichloroacetonitrile (4.04ml), naturally warmed to room temperature and stirred at room temperature for 2h. After the reaction was completed, concentrate with a rotary evaporator, then add n-hexane (100ml) and rinse the precipitate, then filter with a small amount of diatomaceous earth, and concentrate the filtrate to obtain an orange oil, namely PMB ester (8g, 70.2%).

[0036] The synthesis of embodiment 2 formula 2 compounds

[0037] Under nitrogen, methyl trihydroxybutyrate (2.6ml) was first dissolved in dichloromethane (DCM, 56ml), and then PMB ester was dissolved in 56ml DCM. Under nitrogen protection, the diluted PMB ester solution was added dropwise to 1 solution, and then 535 mg of camphorsulfonic acid (CSA) was added, and stirre...

Embodiment 4

[0040] Synthesis (Swern oxidation) of embodiment 4 formula 4 compounds

[0041] Under the conditions of ensuring anhydrous and oxygen-free throughout the reaction process and using nitrogen protection, 1.75ml oxalyl chloride (COCl) 2 It was dissolved in 34ml of DCM, stirred at -60°C, and dimethyl sulfoxide (DMSO, 2.9ml) was added dropwise. After the mixture was stirred at low temperature for 15 min, the compound of formula 3 (2.85 g) was dissolved in DCM (34 ml) and added slowly to the reaction flask. After reacting for 1 h, triethylamine (Et 3 N, 13.22ml), after the addition of the material, the reaction mixture was taken out from the low temperature and placed in an ice-water bath, and then reacted for 2h. After the reaction, add saturated NaCl solution (90ml), extract with DCM (86ml×3), dry over anhydrous sodium sulfate, filter, concentrate and separate by column chromatography (ethyl acetate:petroleum ether=1:10), the The eluate was concentrated to give the compound of ...

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Abstract

The invention provides a method for synthesizing a natural product Tarchonanthuslactone isomer. According to the method, methyl-3-hydroxybutyrate is used as a raw material, and PMB ester protection, LiALH4 reduction, Swern oxidation, Mukaiyama Aldol reaction, ester hydrolysis, Yanaguchi cyclization, de-protection and condensation are performed, so that the natural product Tarchonanthuslactone isomer is obtained. The synthetic route is novel and reasonable in design, the raw materials are cheap and easy to obtain, the operation process is simple and convenient, the reaction condition is mild, the rate is high, side reaction is less, the operation is simple and convenient, and the synthesizing cost is greatly reduced.

Description

technical field [0001] The invention belongs to the field of chemical industry, and in particular relates to a method for synthesizing natural product Tarchonanthuslactone isomers. Background technique [0002] Tarchonanthuslactone, as shown in the following formula (1), is a natural product of polyketone, which was first extracted by Bohlmann from the leaves of a tree called Tarchonanthus trilobus in 1979, and its final shape structure was obtained by Nakata et al. determined by asymmetric synthesis. From the structure of Tarchonanthuslactone, it has an α, β unsaturated δ lactone, and two chiral centers. Tarchonanthuslactone has biological activity, and the study found that it can reduce the blood sugar content of diabetic mice, so it is of great significance to the synthesis of Tarchonanthuslactone and its analogs and isomers for the study of structure-activity relationship, which has attracted many synthetic chemists, Of great interest to biologists and pharmacologists....

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D309/32
CPCC07D309/32
Inventor 王晓季黄飞飞黄双平刘东旺王高鹏王李平覃双林
Owner JIANGXI SCI & TECH NORMAL UNIV
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