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Synthesis method of cephanolide C

A synthetic method and compound technology, which is applied in the field of natural product synthesis, can solve the problems of chemical synthesis method reporting, etc., and achieve the effect of low cost and easy operation

Active Publication Date: 2018-06-08
SHAANXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Up to now, there is no relevant chemical synthesis method reported at home and abroad

Method used

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  • Synthesis method of cephanolide C
  • Synthesis method of cephanolide C
  • Synthesis method of cephanolide C

Examples

Experimental program
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Embodiment 1

[0023]

[0024] 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, then mix with ethyl acetate and saturated The ammonium chloride aqueous 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 16, with a yield of 98%. The structural characterization data are as follows: 1 H NMR (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, 7.2Hz, 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

[0042] 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

[0044] In step 3 of Example 1, the used p-toluenesulfonic acid pyridinium salt is replaced with equimolar p-toluenesulfonic acid, other steps of this step are the same as in Example 1, and the acetal compound shown in formula 7-1 is obtained, and the yield is 58%. Other steps are identical with embodiment 1.

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Abstract

The invention discloses a synthesis method of cephanolide C. The method comprises the steps of taking commercially available 5-bromine-2-methylanisole as a synthesis raw material, performing Ei-ichi Negishi reaction, methoxy contraposition halogenation, and lithium diisopropylamide formylation reaction, allowing a product and 3-pentene-2-ketone to give Robinson cyclization reaction, performing Luche reduction, hydrolysis and esterification reaction to form a lactone compound, performing acid treatment after diisobutyl aluminum hydride reduction to form a Heck reaction precursor, performing palladium catalyzed carbonyl esterification coupling reaction, esterification and carbonyl reduction, then performing sequential oxidation, eemethylation and hydroxyl protection by trifluoromethylsulfonyl via 2,3-dichloro-5,6-dicyan para-quinone and pyridinium chlorochromate, and performing palladium catalyzed removal to achieve chemical synthesis of cephanolide C for the first time. The method has the advantages of concise and efficient synthesis route, easiness and simplicity in operation, low cost and the like, is applicable to massive synthesis of cephanolide C and provides an important material basis for bioactivity evaluation of a natural product, namely cephanolide C.

Description

technical field [0001] The invention belongs to the technical field of synthesis of natural products, and in particular relates to a synthesis method of Cephanolide C. 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 of these ten natural products pro...

Claims

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Application Information

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IPC IPC(8): C07D311/00
Inventor 赵玉明徐伦王超
Owner SHAANXI NORMAL UNIV
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