Supercharge Your Innovation With Domain-Expert AI Agents!

A kind of synthetic method of austrodoral and austrodoric acid

A technology for compounds and natural products, applied in chemical instruments and methods, preparation of carbon-based compounds, preparation of organic compounds, etc., can solve the problems of expensive starting materials or reagents, cumbersome experimental operations, long synthetic routes, etc. Ease of implementation, easy reaction conditions, and desirable yields

Active Publication Date: 2020-07-03
HARBIN INST OF TECH AT WEIHAI
View PDF0 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] At present, there are few reports on the synthetic methods of marine terpenoid natural products austrodoral and austrodoric acid, and most of them have disadvantages such as long synthetic routes, expensive starting materials or reagents, low yields, and cumbersome experimental operations.

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
  • A kind of synthetic method of austrodoral and austrodoric acid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] Embodiment 1: Synthesis of sesquiterpene vicinal diol compound (2, see accompanying drawing).

[0020] At -78°C, first 444mg of sesquiterpene alcohol compound (1, see accompanying drawing, 2.0mmol) was dissolved in 10mL of dichloromethane, and ozone was passed into the reaction system until it turned blue; where N 2 Exhaust the ozone remaining in the reaction system from the reaction system; finally add NaBH to the reaction system 4 (6.0mmol), slowly warming up to room temperature, stirring for 2-3 hours; TLC detection of the end of the reaction, adding 5mL dilute hydrochloric acid to quench the reaction, the reaction solution was extracted with dichloromethane (15mL x 3), combined organic phase, anhydrous sodium sulfate Dry, filter, concentrate, and purify by column chromatography to obtain 452 mg of white solid with a yield of 100%.

Embodiment 2

[0021] Example 2: Synthesis of marine terpenoid natural product austrodoral (see accompanying drawing).

[0022] Take 226mg of sesquiterpene o-diol compound (2, 1.0mmol) and dissolve it in 5mL of dichloromethane, add 0.1mmol of boron trifluoride ether, stir and react at room temperature for 12 hours, TLC detects that the reaction is complete, and then add 10mL of saturated ammonium chloride The solution quenched the reaction, and the reaction solution was extracted with dichloromethane (15mL x 3), the organic phases were combined, dried over anhydrous sodium sulfate, filtered, concentrated, and purified by column chromatography to obtain 177 mg of a colorless oily substance austrodoral, with a yield of 85% . H NMR spectrum 1 H-NMR (400MHz, CDCl 3 )δ:0.83(3H,s),0.85(3H,s),0.86(3H,s),0.94(1H,ddd,J=4.0,13.0,13.0Hz),1.01(3H,s),1.16(1H ,dt,J=4.0,13.0Hz),1.22(1H,dd,J=7.5,12.5Hz),1.27(1H,ddd,J=2.5,11.0,13.0Hz),1.33–1.51(3H,m), 1.52–1.70(3H,m),2.13(1H,ddd,J=6.0,9.5,13.0Hz),9.65(1H...

Embodiment 3

[0023] Example 3: Synthesis of terrestrial terpenoid natural product 8-epi-11-nordriman-9-one (see attached figure).

[0024] Take 226 mg of sesquiterpene vicinal diol compound (2, see attached figure, 1.0 mmol) and dissolve it in 5 mL of dichloromethane, add 2.0 mmol of boron trifluoride ether, stir and react at room temperature for 2 hours, and TLC detects that the reaction is complete. Add 10mL of saturated ammonium chloride solution to quench the reaction, the reaction solution was extracted with dichloromethane (15mL x 3), the organic phases were combined, washed with saturated brine, dried over anhydrous sodium sulfate, filtered, concentrated, and purified by column chromatography to give Color solid 8-epi-11-nordriman-9-one 198 mg, yield 95%. H NMR spectrum 1 H NMR (400MHz, CDCl 3 )δ: 2.68(m, 1H), 2.10(ddd, 1H, J=3.2Hz, J=6.3Hz, J=14.0Hz), 1.72(m, 1H), 1.57(m, 4H), 1.40(d, 1H,J=13.5Hz),1.23(m,3H),1.14(s,3H),1.09(m,1H),0.98(d,3H,J=6.4Hz),0.93(s,3H),0.88( s,3H); C NMR...

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 present invention relates to a marine terpene natural product austrodoral, austrodoric acid and land terpene natural product 8- epi The synthetic method of ‑11‑nordriman‑9‑one belongs to the field of chemical synthesis. The present invention prepares sesquiterpene vicinal diols through the selective ozonation reaction of sesquiterpene alcohols, and then synthesizes the terrestrial terpene natural product 8‑ epi ‑11‑nordriman‑9‑one and austrodoral, a natural product of marine terpene, synthesized austrodoric acid, a natural product of marine terpene, through the oxidation reaction of austrodoral. The invention has the characteristics of low production cost, simple process conditions, easy control, suitability for industrialized production, high total yield and the like.

Description

technical field [0001] The present invention relates to a kind of synthetic method of austrodoral and austrodoric acid Background technique [0002] Marine terpenoid natural products austrodoral and austrodoric acid (see attached photo) are metabolites isolated and extracted from A. kerguelenensis in Terra Nova Bay, Antarctica in 2003, and have a new carbon skeleton (Tetrahedron letters, 2003, 44 , 1495–1498). Marine terpenoid natural products austrodoral and austrodoric acid belong to the austrodorane class of natural products, which have antifungal, antimicrobial, antifeedant and antitumor activities (Tetrahedron, 2007, 63, 11943–11951). Marine terpenoid natural products austrodoral and austrodoric acid are rare in marine organisms and difficult to separate. It is particularly necessary to explore a suitable synthesis method, which is conducive to further study of their biological characteristics. [0003] At present, there are few reports on the synthetic methods of mar...

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): C07C61/13C07C51/16C07C47/347C07C45/52C07C49/447
CPCC07C29/50C07C45/52C07C51/16C07C61/13C07C47/347C07C49/447C07C35/36
Inventor 王军利吴彦超李超逸王龙飞张振国戴春阳沈至仑李惠静
Owner HARBIN INST OF TECH AT WEIHAI
Features
  • R&D
  • Intellectual Property
  • Life Sciences
  • Materials
  • Tech Scout
Why Patsnap Eureka
  • Unparalleled Data Quality
  • Higher Quality Content
  • 60% Fewer Hallucinations
Social media
Patsnap Eureka Blog
Learn More

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

© 2025 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com