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

Method for preparing anomalous methyl ent-isocopalate

A technology of reaction and organic acid, applied in the field of preparation of tricyclic diterpenoids, can solve the problems of low total yield, lengthy synthesis route and the like

Inactive Publication Date: 2009-11-04
EAST CHINA UNIV OF SCI & TECH
View PDF0 Cites 2 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] In summary, the existing methods for preparing methyl ent-isocopalate have the disadvantages of long synthetic routes and low overall yields

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
  • Method for preparing anomalous methyl ent-isocopalate
  • Method for preparing anomalous methyl ent-isocopalate
  • Method for preparing anomalous methyl ent-isocopalate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment

[0025] Preparation of Compound 2:

[0026]

[0027] Compound 1 (3.1g, 0.01mol) was dissolved in acetone (100ml) solution, potassium permanganate (7.9g, 0.05mol) and anhydrous sodium carbonate (8.5g, 0.08mol) were added in batches successively, and then Stirring was continued for 6 hours. After the reaction, the reaction solution was filtered through diatomaceous earth, the filter cake was washed with ethyl acetate, and the mother liquor was concentrated to obtain 2.5 g of a white solid crude product with a yield of 88%.

[0028] The crude product can be directly used in the next reaction without purification; it can also be recrystallized and purified with the following single or mixed solvents. The recrystallization solvent can be: a single solvent or a mixed solvent of petroleum ether, ether, n-hexane, cyclohexane, acetone, ethyl acetate, methylene chloride, chloroform, benzene or toluene.

[0029] Preparation of compound 3:

[0030]

[0031] Compound 2 (2.8g, 0.01m...

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 relates to a method for preparing anomalous methyl ent-isocopalate, which comprises the main step that sclareol as a raw material is prepared into a target product through oxidation reaction, elimination reaction, Wittig-Horner reaction and ring-closure reaction with organic acid in turn. The preparation method has the advantages of compact synthetic route, mild reaction condition, simple and convenient operation (an intermediate does not need to be purified), high yield (the total yield can reach 55 percent), environmental protection and the like, and is a method for preparing methyl ent-isocopalate with commercial value.

Description

technical field [0001] The present invention relates to a kind of preparation method of tricyclic diterpenoid compound, specifically, relate to a kind of preparation method of iso-trans [wanggu][wangba] acid methyl ester (methyl ent-isocopalate). Background technique [0002] Spongiane diterpenoids are biologically active natural products. Because of its wide range of biological activities (including antifeedant, antifungal, antibacterial, antiviral, antitumor, antihypertensive and anti-inflammatory and other biological activities), it has attracted more and more research interests of scientists. [0003] Since the tricyclic diterpenoid methyl ent-isocopalate (methyl isoanticopalate) has a tricyclic structure and a special chiral center, it is an ideal precursor for the preparation of natural products of the sponge (Spongiane) family, and is also a key intermediate for the synthesis of various terpenoids. body. [0004] So far, there are existing methods for preparing isot...

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 Applications(China)
IPC IPC(8): C07C69/753C07C67/333
Inventor 曾步兵华嗣恺
Owner EAST CHINA UNIV OF SCI & TECH
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