A method for the total synthesis of petrosiol E

A technology of total synthesis and intermediates, applied in the fields of organic chemistry, bulk chemical production, hydrolysis preparation, etc., can solve the problems of difficulty in obtaining Petrosiol-like natural products, difficult to meet the needs of chemical properties and biological activity research, etc. Prospects for industrial production, easy operation, mild reaction conditions

Active Publication Date: 2020-06-19
RES CENT FOR ECO ENVIRONMENTAL SCI THE CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] Although Petrosiol-like natural products have significant biological activity, it is very difficult to obtain Petrosiol-like natural products from nature. According to the report of the M.Ojika research group, only 0.9 mg of PetrosiolE can be obtained from 1.2 kg of sponge Petrosistrongylata.
Obviously, relying solely on natural products, it is difficult to meet the needs of chemical properties and biological activity research
There are currently no reports on the total synthesis of PetrosiolE

Method used

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  • A method for the total synthesis of petrosiol E
  • A method for the total synthesis of petrosiol E
  • A method for the total synthesis of petrosiol E

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Experimental program
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Embodiment Construction

[0021] The following provides an embodiment of the present invention:

[0022] Synthesis of compound 1:

[0023] Under the condition of -78℃, the tetrahydrofuran solution of isobutylmagnesium bromide (1mol / L, 3.7eqv) and the tetrahydrofuran solution of cuprous iodide (0.1mol / L, 0.03eqv) were added dropwise to the 11-bromo ten One alcohol (1eqv) in tetrahydrofuran solution, react overnight at room temperature, add saturated ammonium chloride solution to quench the reaction, extract with ethyl acetate, wash the organic phase with water, wash with saturated sodium bicarbonate solution, wash with brine, dry, and evaporate to dryness. The crude product of body 1.

[0024] Synthesis of compound 2:

[0025] Intermediate 1 (1eqv), triphenylphosphine (1.5eqv), and imidazole (1.5eqv) were dissolved in toluene, stirred vigorously, iodine (3eqv) was added at 0°C, and the reaction was heated for 2 hours. Wash with saturated sodium thiosulfate solution, extract with ether, wash the organic phase ...

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Abstract

The invention aims to provide a novel organic chemical total synthetic method of a natural product, petrosiol E. D-xylose is adopted as the raw material, and the total synthesis of petrosiol E is enantio-selectively completed. The route has the following advantages: (1) the raw material is low in price and easy to get, and the used reagents and solvents are common industrial reagents; (2) the operation is easy and convenient, the reaction condition is mild, the yield is high, and the method is applicable to large-scale preparation; (3) the obtained petrosiol E is the same as the natural product in spectroscopic data and optical rotation data. The invention has the characteristic that the method comprises the steps as follows (referring to the description).

Description

Technical field [0001] The invention relates to a new method for the total synthesis of natural product petrosiolE in organic chemistry, which belongs to the technical category of organic chemistry. Background technique [0002] Petrosiol natural products were isolated from the sponge Petrosiastrongylata in 2013 by the M.Ojika research team in Japan. Studies have shown that it has significant neurotrophic activity and may be used to treat neurological diseases; it may also be used to prevent and treat vascular diseases such as Atherosclerosis and so on. [0003] Although Petrosiol natural products have significant biological activity, it is very difficult to obtain Petrosiol natural products from nature. According to M. Ojika's research group, only 0.9 mg of Petrosiol E can be obtained from 1.2 kg of sponge Petrosiastrongylata. Obviously, only relying on natural products can hardly meet the needs of chemical properties and biological activity research. So far, only the P.Srihari ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C33/04C07C29/10
CPCY02P20/55
Inventor 杜宇国王琳琳刘军刘义
Owner RES CENT FOR ECO ENVIRONMENTAL SCI THE CHINESE ACAD OF SCI
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