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Method for preparing guaipyridine type sesquiterpenoid alkaloid

A technology for sesquiterpenoids and alkaloids, which is applied in the field of preparing guaiacol-type sesquiterpene alkaloids

Active Publication Date: 2021-09-17
XINJIANG TECHN INST OF PHYSICS & CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In 2020, James R.Vyvyan's research group reported that the enantiomers of Rupestine D had been synthesized, and epimers existed at the same time. During the separation process, a preparative chiral column was used, and only milligram-level separations could be performed.

Method used

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  • Method for preparing guaipyridine type sesquiterpenoid alkaloid
  • Method for preparing guaipyridine type sesquiterpenoid alkaloid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Preparation of compound 1

[0034] Dissolve the raw material citronellol 100g, 640mmol in 1.40L of dichloromethane, add 185g, 704mmol of triphenylphosphine at 0°C, add 95.9g, 1410mmol of imidazole after 5min, slowly add 179g, 704mmol of iodine in batches after 30min, React at room temperature for 5 hours, add saturated sodium thiosulfate solution to quench, dichloromethane was evaporated to dryness, petroleum ether was added, pulped, filtered with suction, the filtrate was evaporated to dryness, and purified to obtain compound 1 named (S)-8-iodo-2, 6-Dimethyloct-2-ene 162g, yield 95%;

[0035] 1 H NMR (400MHz, CDCl 3 )δ5.11–5.07(m,1H),3.29–3.20(m,1H),3.20–3.08(m,1H),2.09–1.80(m,3H),1.68(s,3H),1.67–1.62( m,1H),1.60(s,3H),1.59–1.48(m,1H),1.40–1.26(m,1H),1.22–1.12(m,1H),0.89(d,J=6.6Hz,3H) .

Embodiment 2

[0037] Preparation of compound 2

[0038] Compound 1 obtained in Example 1 was (S)-8-iodo-2,6-dimethyloct-2-ene 162g, 610mmol was dissolved in 1.50L tetrahydrofuran, and potassium tert-butoxide 75.3 g, 671mmol, reacted overnight, quenched by adding saturated ammonium chloride, extracted, concentrated, and purified to obtain compound 2 named (S)-3,7-dimethyloctadiene-1,6-diene, also known as Citronellene 80.9g, yield 96%;

[0039] 1 H NMR (400MHz, CDCl 3 )δ5.75–5.66(ddd,1H),5.13–5.08(m,1H),4.98–4.90(m,2H),2.16–2.09(m,1H),2.00–1.93(m,2H),1.69( s, 3H), 1.60 (s, 3H), 1.35–1.29 (m, 2H), 0.99 (d, J=6.8Hz, 3H).

Embodiment 3

[0041] Preparation of compound 3

[0042] 20.4g of selenium dioxide, 148mmol, 42g of tert-butanol peroxide, 326mmol, and 70% aqueous solution were dissolved in 600mL of dichloromethane, reacted at room temperature for 30 minutes, and then added the compound 2 obtained in Example 2 to be (S)-3, 7-Dimethyloctadiene-1,6-diene, continued to react for 2 hours, quenched by adding saturated sodium thiosulfate, extracted, concentrated, and purified to obtain compound 3 named (S, E)-2,6 -Dimethyloctyl-2,7-dien-1-ol 15.9g, yield 70%;

[0043] 1 H NMR (400MHz, CDCl 3 )δ5.67(ddd,J=17.5,10.3,7.5Hz,1H),5.38–5.34(m,1H),4.96–4.88(m,2H),3.95(d,J=6.0Hz,2H),2.14 -2.07 (m, 1H), 2.05 - 1.92 (m, 3H), 1.63 (s, 2H), 1.32 (qd, J=7.2, 1.5Hz, 2H), 0.97 (d, J=6.8Hz, 3H).

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Abstract

The invention relates to a method for preparing guaipyridine type sesquiterpenoid alkaloids. The method is characterized in that a plurality of guaipyridine type sesquiterpenoid alkaloids are obtained by changing segments of intermediates and changing subsequent functional groups, and asymmetric total synthesis of rupestine D and guaipyridine is realized. The method has the characteristic of flexible divergent synthesis, and provides a new way for subsequent screening of compounds with better biological activity. Rupestine D and guaipydine, which are obtained by the method, are subjected to optical rotation, nuclear magnetic data, high-resolution mass spectrum, single crystal and other contrasts with a naturally separated sample, so that the chemical structure and the spatial configuration of the rupestine D and guaipydine are determined.

Description

technical field [0001] The invention belongs to the technical field of pharmaceutical preparations, and relates to a method for preparing guaiphenidin-type sesquiterpene alkaloids. Background technique [0002] Xinjiang Yizhi Artemisia is the whole herb of Artemisia rupestris L. of the genus Artemisia in the Compositae family. It is also known as Snow Artemisia, Rock Artemisia, and Staghorn Artemisia. It is produced in Tianshan and Altai Mountains in Xinjiang. It has a long history and has biological activities such as anti-allergic, anti-viral, anti-inflammatory, anti-bacterial, liver protection, and anti-cancer. It is used to treat symptoms such as colds, colds, bruises, snake bites, and urticaria. [0003] In 2008, the research group of Aji Aikebaier Aisa isolated five novel guaiacol-type sesquiterpene alkaloids for the first time from Artemisia argyi in Xinjiang. In 2012, the research group again isolated eight compounds of this type from Artemisia argyi. [0004] Stru...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D221/04
CPCC07D221/04
Inventor 阿吉艾克拜尔·艾萨张存王边琳
Owner XINJIANG TECHN INST OF PHYSICS & CHEM CHINESE ACAD OF SCI