Al technical title is built by PatSnap Al team. It summarizes the technical point description of the patent document.
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
View PDF0 Cites 0 Cited by
Summary
Abstract
Description
Claims
Application Information
AI Technical Summary
This helps you quickly interpret patents by identifying the three key elements:
Problems solved by technology
Method used
Benefits of technology
Problems solved by technology
Up to now, there is no relevant chemical s
Method used
the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more
Image
Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
Click on the blue label to locate the original text in one second.
Reading with bidirectional positioning of images and text.
Smart Image
Examples
Experimental program
Comparison scheme
Effect test
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.
the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more
PUM
Login to view more
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
the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more
Application Information
Patent Timeline
Application Date:The date an application was filed.
Publication Date:The date a patent or application was officially published.
First Publication Date:The earliest publication date of a patent with the same application number.
Issue Date:Publication date of the patent grant document.
PCT Entry Date:The Entry date of PCT National Phase.
Estimated Expiry Date:The statutory expiry date of a patent right according to the Patent Law, and it is the longest term of protection that the patent right can achieve without the termination of the patent right due to other reasons(Term extension factor has been taken into account ).
Invalid Date:Actual expiry date is based on effective date or publication date of legal transaction data of invalid patent.