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Total synthesis method for rape pollen alkali A and caper alkali B and analogues thereof

A technology of rapeseed pollen and caperine, which is applied to chemical instruments and methods, sugar derivatives, sugar derivatives, etc., can solve the problems of high price and large amount of original drug, and achieve low environmental pollution and high yield Effect

Inactive Publication Date: 2015-05-20
DALIAN UNIV OF TECH
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Extracting and separating glycopyrrole alkaloids from natural medicinal materials requires a large amount of raw materials and is expensive

Method used

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  • Total synthesis method for rape pollen alkali A and caper alkali B and analogues thereof
  • Total synthesis method for rape pollen alkali A and caper alkali B and analogues thereof
  • Total synthesis method for rape pollen alkali A and caper alkali B and analogues thereof

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Embodiment Construction

[0038] The present invention will be described in further detail below in conjunction with the examples, but the embodiments of the present invention are not limited thereto.

[0039] Weigh 15.19g of sodium hydride and put it in a 500mL three-necked flask, dissolve it with 50mL of DMF, measure 10mL of pyrrole, dissolve it with 60mL of DMF, slowly add the DMF solution of pyrrole (about 3 seconds a drop) in the flask under ice bath, after the drop Weigh 30.58g of compound II, dissolve it in 60mL of DMF, slowly add the raw material solution dropwise (about 3 seconds per drop) into a three-necked flask under ice bath, transfer to a 40°C oil bath to react for 1h, raise the temperature of the oil bath to 135°C, React for 4-5 days, TLC (P:E=3:1) detects that the reaction is basically complete, add a small amount of methanol to neutralize NaH until no bubbles are formed, distill off DMF under reduced pressure, extract the reaction solution with ethyl acetate multiple times, and the org...

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Abstract

The invention provides a total synthesis method for natural products such as rape pollen alkali A and caper alkali B with the activity of delaying cell aging. The method comprises the following steps: taking fructose as an initial raw material, performing tosylate formation, pyrrole substitution, pyrrole bi-hydroxymethylation, oxidation and selective deprotection, reducing and performing acid catalysis on intramolecular ketalation, carrying out a Barton-McCombie deoxidation reaction and a benzyl removal reaction, thereby obtaining the final products such as the rape pollen alkali A and caper alkali B. According to the total synthesis method disclosed by the invention, cheap and readily available raw materials are adopted, the environmental pollution caused by the reaction solvents and reagents is slight, the yield is high, and the synthesized alkaloids and analogues thereof can be used for developing novel anti-inflammatory agents and anti-aging drugs.

Description

technical field [0001] The invention belongs to the field of chemical synthesis and relates to a method for the total synthesis of rapeseed pollen A, caperine B and analogs. technical background [0002] Pyrrolose compounds are widely used in different medical fields, such as the treatment of neurological diseases, etc. The U.S. Food and Drug Administration approved Cuvposa (glycopyrrolate) oral solution on July 28, 2010 to treat children aged 3 to 16 years old. Chronic severe drooling caused by neurological disorders. In recent years, a unique class of glycopyrrole alkaloids has been found in different parts of various plants. In 2003, Tu Pengfei et al. isolated six new alkaloid compounds from Astragalus membranaceus (Ma Xiaofeng et al. Research on the chemical constituents of Astragalus membranaceus, Shenyang Pharmaceutical University of Science and Technology doctoral dissertation 2003), Wang Changhong et al. reported that in the capers fruit extract, it was found to con...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H19/01C07H1/00
Inventor 赵伟杰李悦青王世盛曹志郭修晗曹雷王柳朱季
Owner DALIAN UNIV OF TECH
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