Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Preparation method of natural alkaloid lundurine A-C

An alkaloid, natural technology, applied in the direction of organic chemistry, etc., can solve the problems of long reaction steps, harsh reaction conditions, expensive reaction conditions of reaction reagents, etc., and achieve the effect of low cost

Active Publication Date: 2019-06-28
NANJING UNIV
View PDF0 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] The purpose of the present invention is to provide a new method for the preparation of alkaloids Lundurine A-C from simple and easy-to-get commercial raw materials, and partially solve the limitations of synthesizing Lundurine A-C in the literature route, such as long reaction steps, expensive reaction reagents and reaction Harsh conditions, etc.

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Preparation method of natural alkaloid lundurine A-C
  • Preparation method of natural alkaloid lundurine A-C
  • Preparation method of natural alkaloid lundurine A-C

Examples

Experimental program
Comparison scheme
Effect test

Embodiment Construction

[0010] Preparation of compound TMS-based lactone II (intermediate II):

[0011] Add a stirring bar to a 25mL round bottom flask, replace nitrogen, add trimethylsilylacetylene (4.4mL, 11mmol), anhydrous and oxygen-free THF (15mL), cool at -78°C for 30min, add n-butyllithium (11mmol) dropwise for 30min , -78 ℃ should be 60 minutes. A 100mL round-bottomed flask filled with I (1.28g, 10mmol) was replaced with nitrogen, anhydrous tetrahydrofuran (55mL) was added, lithium reagent was added dropwise to the reaction flask at -78°C for 60 minutes, and reacted at -78°C for 2 hours (thin layer analysis detection). The reaction was quenched with sodium acetate / acetic acid buffer solution (pH=6.5), and extracted with ethyl acetate. The organic phase was washed with water and saturated sodium chloride, and dried over anhydrous sodium sulfate. After filtration, the mother liquor was concentrated under reduced pressure; the concentrate was purified by silica gel column chromatography (petr...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention provides a preparation method of natural alkaloid Lundurine A-C. The preparation method comprises the following steps: taking lactone I as a starting raw material and carrying out carbonyl alkynylation to generate TMS (Tetramethyl Silane) group lactone II; carrying out ring opening on the TMS group lactone II, and removing a TMS group and converting the TMS group lactone II into diol III at the same time; carrying out acetylation on the diol to obtain an ether IV, namely an intermediate IV; under the catalysis of copper salt, selectively enabling propargyl ether of the ether IV and 5-methoxytryptamine to be subjected to amination reaction to generate propargylamine V, namely an intermediate V; carrying out ring closing reaction on the propargylamine V under a neutral thermal condition to generate lactam VI; catalyzing the lactam VI by utilizing a monovalent gold reagent to generate azaoctane VII; carrying out intramolecular [3+2] ring addition-denitrification reaction on tosylhydrazone XI to generate an intermediate XII; carrying out carbonyl alpha-site selenylation and oxidization elimination reaction on amide of the XII to generate Lundurine A; directly reducing the amide of the intermediate XII to generate Lundurine C.

Description

technical field [0001] The invention relates to a method for preparing natural alkaloids Lundurine A, Lundurine B and Lundurine C, belonging to the technical field of resources, medicine and chemical industry. Background technique [0002] Lundurine A-D is a natural indole alkaloid isolated by Kam from the genus Malaysia. Its molecular structure contains units such as indoline, azacyclooctane, cyclohexane, dihydropyrrole and cyclopropane. Biological activity tests showed that: lundurine B and D had significant cytotoxicity to B16 melanoma (IC50 value 2.8g / mL); lundurine B could effectively overcome the drug resistance of KB cells to vinblastine and other drugs (Kam, T.-S.; Yoganathan, K.; Chuah, C.-H. Tetrahedron Lett.1995, 36, 759-762. Kam, T.-S.; Lim, K.-H.; Yoganathan, K.; M.; Komiyama, K. Tetrahedron 2004, 60, 10739-10745.). [0003] [0004] This polycyclic spirocyclic alkaloid containing multiple quaternary carbon centers is challenging to synthesize, and the key ...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Patents(China)
IPC IPC(8): C07D487/20
CPCC07D487/20
Inventor 王少仲郭涛
Owner NANJING UNIV
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com