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

Synthetic method of Reziya base tetracyclic skeleton

A technology of Reziya base and synthesis method, which is applied in the field of synthesizing Reziya base tetracyclic skeleton, can solve problems such as large tension and complex structure, and achieve the effects of efficient route, simple operation steps and economical steps.

Active Publication Date: 2019-09-10
EAST CHINA NORMAL UNIV
View PDF1 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Complex structure, high tension

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
  • Synthetic method of Reziya base tetracyclic skeleton
  • Synthetic method of Reziya base tetracyclic skeleton
  • Synthetic method of Reziya base tetracyclic skeleton

Examples

Experimental program
Comparison scheme
Effect test

Embodiment Construction

[0036] The present invention will be described in detail below.

[0037] 1) Compound 1 (1.9g, 5.32mmol, 1.0equiv.), silver oxide (3.8g, 16mmol, 3.0equiv.) and tetrabutylammonium iodide (393mg, 1.06mmol, 0.2equiv.) were dissolved in heavy distilled dichloromethane. Then iodomethane (1.66ml, 26.6mmol, 5.0equiv.) was added and reacted overnight at room temperature. Excess methyl iodide was quenched with saturated sodium sulfite, water was added, extracted three times with ethyl acetate, washed with saturated brine, and dried over anhydrous sodium sulfate. The crude product was separated by column to obtain compound 2 (1.67g, 84%, Rf=0.39 (15% ethyl acetate / petroleum ether).

[0038] 1 H NMR (400MHz, CDCl 3 )δ7.41–7.29(m,6H),7.06(dd,J=14.4,3.7Hz,1H),5.53–5.36(m,1H),5.26–5.06(m,2H),4.53(d,J= 46.8Hz, 1H), 4.24–4.08(m, 1H), 3.89(d, J=22.3Hz, 1H), 3.74(s, 3H), 3.61–3.44(m, 4H), 3.31(s, 2H), 1.89(dd,J=27.6,12.6Hz,1H),1.77(dd,J=6.8,2.1Hz,3H).

[0039] 13 C NMR (101MHz, CDCl 3 )...

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 discloses synthesis methods of a rhazimine tetracyclic skeleton. One of the synthesis methods adopts the following linear synthesis route: gamma-hydroxy-alpha,beta-unsaturated ester having a [3,3,1] ring system structure is adopted an initial raw material; a methanol group protects the hydroxyl group of allyl alcohol, and deconjugation alkylation is creatively used to achieve the migration of a double bond and construct a whole carbon quaternary carbon center; lithium tetrafluoroborate undergoes silicon deprotection and alkenyl ether structure hydrolysis; an aldehydic carbonyl group obtained by oxidizing a primary alcohol and o-iodoaniline undergo reducing amination, and a ketocarbonyl group is reduced; a secondary alcohol is oxidized; and the rhazimine tetracyclic skeleton is constructed through the alpha-position coupling of the carbonyl group. The other one of the synthesis methods adopts the following convergent synthesis route: a methyl-protected allyl alcohol structure and chloride connected with the o-iodoanide fragment undergoes deconjugation alkylation, and then intramolecular coupling is carried out to construct the rhazimine tetracyclic skeleton. The synthesis methods have the advantages of simple operating steps, low requirements of reaction conditions, and high-efficiency synthesis of the target compound.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a method for synthesizing the tetracyclic skeleton of raizia base. Background technique [0002] Plants rich in akuammiline alkaloids or their extracts are widely used as folk medicines in many countries and regions. It is precisely because of the medicinal value of these plants or their extracts that aroused the research interests of natural product isolates and pharmacologists. Since the content of akumilin alkaloids is the largest, the akumilin alkaloids are collectively referred to as the natural products of this family. Scientific research has found that acumilin alkaloids have good biological activities such as anti-cancer, bactericidal, anti-inflammatory, cough-relieving, and anti-malarial. Through subsequent medicinal chemistry research, acumilin alkaloids may show their charm in pharmaceutical applications. [0003] Structurally, this class of al...

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): C07D471/08
Inventor 纪跃王丹高栓虎
Owner EAST CHINA NORMAL 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