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Preparation method of tetracyclic terpene compound

A compound, C1-C12 technology, applied in the field of preparation of tetracyclic terpenoids, can solve the problems of ecological damage, low yield, single product, etc.

Inactive Publication Date: 2012-09-12
INST OF CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Terpenoid 1 is derived from the leaves of natural plants. However, the extraction of such compounds by this method is limited by the characteristics of low yield, single product, and ecological damage.

Method used

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  • Preparation method of tetracyclic terpene compound
  • Preparation method of tetracyclic terpene compound
  • Preparation method of tetracyclic terpene compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0082] The preparation of embodiment 1, tetracyclic terpenoids

[0083] The structural formulas of the prepared tetracyclic terpenoids are shown in formula 1-a, formula 1-b, and formula 1-c.

[0084]

[0085] Formula 2-a Formula 3-a Formula 3 / 4-a

[0086]

[0087] Formula 4-a Formula 5-a Formula 6-a

[0088]

[0089] Formula 7-a Formula 1-a Formula 1-b

[0090]

[0091] Formula 1-c

[0092]

[0093] In the above formula, "TBS" represents "tert-butyldimethylsilyl".

[0094] The compound shown in 5.85g formula (2-a) and 6.01g ethyl acrylate are dissolved in 40mL chloroform, add the compound shown in 0.90g formula (15) (compound shown in formula (2-a), ethyl acrylate and formula The molar fraction ratio of the compound shown in (15) is 1: 3: 0.1), reacted for 60 hours at 25° C., concentrated, and crossed a flash chromatographic column to obtain the compound shown in 5.65g formula (3-a) (72%, 90% ee ) (analytical conditions: high performance liquid chromatograp...

Embodiment 2

[0106] Embodiment 2, the preparation of tetracyclic terpenoids

[0107] The structural formulas of the prepared tetracyclic terpenoids are shown in formula 1-d, formula 1-e, formula 1-f, and formula 1-g.

[0108]

[0109] Formula 1-a Formula 1-d Formula 1-e

[0110]

[0111] Formula 1-f Formula 1-g

[0112] Under nitrogen, dissolve 0.495g of the compound represented by formula (1-a) in 11mL of dichloromethane, place it in a -78°C reaction bath, add 2.8mL of diisobutylaluminum hydride (1M n-hexane solution) , moved to an ice-water bath to react for 1 hour. Add 0.5 mL of methanol to quench the reaction, add 20 mL of saturated sodium potassium tartrate solution, stir at room temperature for 0.5 hours, extract with dichloromethane (10 mL x 3), combine the organic phases, dry over anhydrous magnesium sulfate, filter, concentrate, and pass through a flash chromatography column Purification gave 0.346 g of the compound represented by formula (1-d) (78%) as a colorless oil. ...

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PUM

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Abstract

The invention discloses a tetracyclic terpene compound and a preparation method thereof. The structural formula of the compound is shown as a formula I. The preparation method comprises the following steps of: (1) reacting a compound shown as a formula 2 with an acrylic acid derivative in the presence of a chiral alkali; (2) performing a selective reduction reaction on the obtained product in the presence of a reducing agent and a heptahydrate of cerous chloride, and protecting hydroxyl; (3) performing a reduction reaction on the obtained product; (4) performing Swern oxidation on the obtained product, and performing a Wittig reaction in the presence of hexamethylphosphoric triamide; (5) performing an intra-molecular olefin metathesis reaction on the obtained product under the catalytic action of a Grubbs second generation catalyst to obtain spiro-olefin; and (6) performing a selective cyclopropanation reaction on the spiro-olefin and a diazo compound in the presence of a metal catalyst and a chiral ligand to obtain a compound shown as a formula 1. The method has the advantages of simple steps, mild reaction conditions, high yield, convenience for amplifying, convenience for deriving a product and high industrial production potential.

Description

technical field [0001] The invention relates to a preparation method of tetracyclic terpenoids. Background technique [0002] In 2010, Guo Yuexiong's research team extracted a class of terpenoids (1) (Cryptotrione) with a new carbon skeleton from the leaves of Cryptomeria japonica collected in Xitou, Taiwan (Org.Lett.2010, 12, 2786-2789). The biological activity test of this terpenoid compound showed that: 1 showed better biological activity (IC 50 =6.44±2.33μM), and its anticancer activity (IC 50 =2.0 μM), so its research and transformation is expected to be used as a lead compound for the development of new anticancer clinical drugs. [0003] [0004] Terpenoid 1 is derived from the leaves of natural plants. However, the extraction of such compounds by this method is limited by the characteristics of low yield, single product, and ecological damage. By means of chemical synthesis, not only can a large number of such compounds be prepared, but also derivatives of suc...

Claims

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Application Information

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IPC IPC(8): C07F7/18C07C69/757C07C67/31C07C217/74C07C213/00
Inventor 史一安陈松荣潮冯鹏举李松磊
Owner INST OF CHEM CHINESE ACAD OF SCI
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