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Polysubstituted decahydronaphthalene compound, synthesis method and uses thereof

A compound, decalin technology, applied in the field of multi-substituted decalin compounds, can solve problems such as complex oxidative degradation, and achieve the effects of simple and easy method, high yield and low cost

Inactive Publication Date: 2009-02-18
CHENGDU INST OF BIOLOGY CHINESE ACAD OF S
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But when synthesizing ambroxan, the oxidative degradation of sclareol side chain is still relatively complicated, and metal ions such as Cr(VI), Mn(VII) are used as oxidizing agents to produce Cr(III), Mn(II) and other harmful substances. waste; in addition, the acid-catalyzed dehydration-cyclization process easily leads to the isomerization of Ambrox and the formation of other by-products

Method used

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  • Polysubstituted decahydronaphthalene compound, synthesis method and uses thereof
  • Polysubstituted decahydronaphthalene compound, synthesis method and uses thereof
  • Polysubstituted decahydronaphthalene compound, synthesis method and uses thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Example 1 With oleanolic acid AB (R 4 For β methyl) fragments as raw materials, synthetic compounds 2 and 3

[0030] 1) Preparation of Compound 2:

[0031]

[0032] LiAlH under the protection of argon 4 (49 mg, 1.3 mmol) was added into 5 mL of anhydrous THF dissolved in compound 1 (100 mg, 0.32 mmol) at room temperature, refluxed for 4 hours under the protection of argon, and then cooled to room temperature. Then 50 μL of water, 50 μL of 15% NaOH solution, and 150 μL of water were added sequentially to quench the reaction. After filtering and washing with THF three times, the combined filtrates were concentrated and then subjected to silica gel column chromatography (petroleum ether-acetone, 2:1) to obtain compound 2 (79 mg, 79%).

[0033] 2) Preparation of compound 4:

[0034]

[0035] Compound 1 (50 mg, 0.16 mmol) was added into the reaction flask, replaced with argon three times, then injected with 10 mL of anhydrous THF, and then injected with 135 μL of a ...

Embodiment 2

[0039] Example 2 With oleanolic acid AB (R 4 For α methyl) fragments as raw materials, synthetic compounds 2 and 3

[0040] Using the operation steps described in Example 1, the compound 2 and 3 obtained are as follows:

[0041]

Embodiment 3

[0042] Example 3 Using the AB fragment of maslinic acid as raw material to synthesize compounds 2 and 3

[0043] Using the operation steps described in Example 1, the compound 2 and 3 obtained are as follows:

[0044]

[0045] R 4 = α-methyl or β-methyl

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PUM

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Abstract

The invention belongs to the field of organic chemistry and relates to a polysubstituted decalin compound, and a synthesis method and an application thereof. The structural formula of the polysubstituted decalin compound is shown above. The preparation of the polysubstituted decalin compound includes septs as follows: AB fragment which is obtained by the c-bond cleavage of an oleanane type or an ursolic alkane type pentacyclic triterpenoid compound is treated with different reduction methods to obtain a compound 2 or 3. The polysubstituted decalin compound of the invention is used to synthesize the medicine or the apice and the analogues which contain the structural fragment of the polysubstituted decalin. The invention has the advantages of simplicity, practicability, low cost, high yield and being capable of industrialization.

Description

technical field [0001] The invention belongs to the field of organic chemistry and relates to a multi-substituted decahydronaphthalene compound, its synthesis method and application. Background technique [0002] Polysubstituted decahydronaphthalene structural fragments are important structural units of many natural products such as triterpenes, diterpenes, sesquiterpenes and their analogs. Most of these compounds have biological activities such as anti-tumor, herbicide, anti-fungal, anti-microbial, anti-leukemia and anti-inflammation, and play an important role in the scientific research and industrial production of spices. [0003] In the synthesis of these natural products and their analogs, a decahydronaphthalene fragment is usually constructed and then coupled with other parts, and the synthesis of decahydronaphthalene is one of the important tasks. It is usually obtained through total synthetic construction, semi-synthetic construction or semi-synthetic degradation fr...

Claims

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Application Information

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IPC IPC(8): C07C35/36C07C29/147C07D307/92
Inventor 谢义鹏张国林
Owner CHENGDU INST OF BIOLOGY CHINESE ACAD OF S
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