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A kind of synthetic method of crude torene terpenoid skeleton compound

A technology of a skeleton compound and a synthetic method, applied in the field of synthesis of natural products, can solve problems such as reports on the chemical synthesis method of crude torreya-like diterpenoid natural products, and achieve the effects of simple and efficient synthetic route, easy operation and low cost

Active Publication Date: 2019-12-17
SHAANXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

So far, there have been no reports on the chemical synthesis methods of these ten new crude torreya-like diterpenoid natural products at home and abroad.

Method used

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  • A kind of synthetic method of crude torene terpenoid skeleton compound
  • A kind of synthetic method of crude torene terpenoid skeleton compound
  • A kind of synthetic method of crude torene terpenoid skeleton compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018]

[0019] 1. Add 24.1g (120mmol) of 5-bromo-2-methylanisole shown in formula 1, 539mg (2.4mmol) of palladium acetate, 1.1g (4.8mmol) of S-Phos in a 500mL dry round bottom flask , then add 50mL of degassed tetrahydrofuran, stir at room temperature for 5 minutes under the protection of nitrogen, then add 300mL of 0.6mol / L tetrahydrofuran solution of ethyl 4-bromobutyrate zinc reagent, stir at 50°C for 5 hours, and then use ethyl acetate and saturated chlorine The ammonium chloride solution was extracted, the organic phase was collected, dried over sodium sulfate, spin-dried, and passed through the column with petroleum ether and ethyl acetate to obtain 27.8 g of the compound shown in formula 10, with a yield of 98%. The structural characterization data are as follows: 1 HNMR (600MHz, deuterated chloroform) δ7.07(d, J=7.5Hz, 1H), 6.71(d, J=7.5Hz, 1H), 6.69(s, 1H), 4.16(q, J=7.6, 7.2 Hz, 2H), 3.85(s, 3H), 2.66(t, J=7.7Hz, 2H), 2.36(t, J=7.5Hz, 2H), 2.23(s, 3H), 1.99(p, J=...

Embodiment 2

[0031] In step 2 of Example 1, the 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride used is replaced with equimolar dicyclohexylcarbodiimide, other steps of this step Same as Example 1, the lactone compound represented by formula 5-1 was obtained, and the total yield of the two steps was 57%. Other steps are identical with embodiment 1.

Embodiment 3

[0033] In step 3 of Example 1, the pyridinium p-toluenesulfonic acid used is replaced with equimolar p-toluenesulfonic acid, and the other steps of this step are the same as in Example 1 to obtain the acetal compound shown in Formula 7-1, with a yield of 58%. Other steps are identical with embodiment 1.

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Abstract

The invention discloses a synthesis method of a cephalotaxus sinensis terpenoid framework compound. The method comprises the following steps: commercially available 2-methyl-5-bromoanisole as a synthetic raw material is subjected to Ei-ichi Negishi reaction for para-halogenation with a methoxyl group, then a product is subjected to formylation reaction with lithium diisopropylamide, and a 1,3-dicarbonyl compound is obtained; the 1,3-dicarbonyl compound is subjected to a Robinson cyclization reaction with 3-pentene-2-one, and a lactone compound is obtained through Luche reduction, hydrolysis and esterification reaction; acid treatment is performed after reduction by diisobutylaluminum hydride, a Heck reaction precursor is obtained and subjected to palladium-catalyzed carbonyl esterificationcoupling reaction, and chemical synthesis of the crude cephalotaxus sinensis terpenoid framework compound is achieved by esterification. The synthetic route has the advantages of being simple, efficient, convenient to operate, low in cost and the like, and the method is applicable to large-scale synthesis of the cephalotaxus sinensis terpenoid framework compound, and provides an important experimental basis for chemical synthesis of cephalotaxus sinensis terpenoid natural products.

Description

technical field [0001] The invention belongs to the technical field of synthesis of natural products, and in particular relates to a method for synthesizing crude torene terpenoid skeleton compounds. Background technique [0002] Torreyaceae plants provide us with a large family of natural products with various biological characteristics and diverse structures. Of particular importance are natural products with antitumor activity. Among these secondary metabolites, diterpenoid natural products have intriguing structural features. In 1978, the first diterpenoid natural product of Torreya genus, Torreya lactone, was isolated and discovered by Buta et al. from the seeds of Torreya, and it was proved to have good anti-tumor activity. In 2017, Yue Jianmin, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, and others extracted ten new diterpenoid natural products Cephanolide (A-J) from crude Torreya biscuits (J. Nat. Prod., 2017, 80, 3159-3166). The discovery o...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D311/00
CPCC07D311/00
Inventor 赵玉明王超徐伦
Owner SHAANXI NORMAL UNIV
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