Synthesis method of natural product (-)-newbouldine

A synthetic method and technology of natural products, applied in the direction of organic chemistry, etc., can solve the problems of harsh reaction conditions, low yield, difficult post-processing, etc., and achieve the effects of mild reaction conditions, easy post-processing, and simple operation

A synthetic method and technology of natural products, applied in the direction of organic chemistry, etc., can solve the problems of harsh reaction conditions, low yield, difficult post-processing, etc., and achieve the effects of mild reaction conditions, easy post-processing, and simple operation

CN109956948AInactive Publication Date: 2019-07-02SHAANXI NORMAL UNIV
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  • Synthesis method of natural product (-)-newbouldine
  • Synthesis method of natural product (-)-newbouldine
  • Synthesis method of natural product (-)-newbouldine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025]

[0026] 1. Under the protection of argon, dissolve 2.6g (10mmol) of compound 1 in redistilled tetrahydrofuran, add 14mL of 1mol / L diethyl ether solution of phenylmagnesium bromide dropwise at 0°C, and stir for 30 minutes after the dropwise addition , and then the reaction was quenched by adding saturated aqueous ammonium chloride. The resulting mixture was extracted 3 times with ether, washed 3 times with saturated brine, dried over anhydrous sodium sulfate, concentrated with a rotary evaporator, and finally subjected to column chromatography (ethyl acetate:petroleum ether=5:100~20:100, v / v) Purification to obtain 1.72g of white solid compound 2, whose chemical name is tert-butyl (S)-2-benzoylpyrrole-1-carbonate, the yield is 62%, and the structural characterization data are as follows: 1 H NMR (600MHz, CDCl 3 )δ7.97(dd, J=21.2,7.4Hz,1.97H),7.57(dt,J=21.2,7.4Hz,1H),7.47(dt,J=20.0,7.7Hz,2H),5.37-5.31( m,0.39H),5.20(dd,J=8.8,3.8Hz,0.59H),3.72-3.61(m,1H),3.56(dt,J=1...

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Abstract

The invention discloses a synthesis method of a natural product (-)-newbolline. With optically-active Boc protected pyrrolidine formamide as a raw material, five chemical conversion processes are successively carried out, namely, a Grignard reaction, a Wittig reaction, a hydroboration-oxidation reaction, a hydroxyl azide reaction and an iron-catalyzed N-N cyclization reaction, so as to realize high-efficiency simple total synthesis of the natural product (-)-newbolline. The synthesis method has the advantages of simple operation, mild reaction conditions, easy post-treatment and high yield ofthe target compound. Compared with a reported synthetic route, the method disclosed by the invention does not need to use highly toxic cuprous cyanide, a large amount of titanium trichloride and a large amount of strong corrosive concentrated hydrochloric acid, and the dosage of the key N-N forming reaction catalyst in the last step only needs 0.02-0.05 chemical equivalent. Therefore, the invention provides an important method for large-scale preparation of the natural product (-)-newbolone.

Description

technical field [0001] The invention belongs to the technical field of synthesis of natural products, in particular to a synthesis method of natural product (-)-newbouldine. Background technique [0002] Natural products containing N-N bonds are rare in nature. The alkaloid newbouldine containing a hydrazone functional group in the molecule was first isolated in 1993 from the Bignoniaceae plant Newbouldia laevis in Ivory Coast, West Africa and other places (Burkill, H.M. The useful Plants of West tropical Africa; Royal Botanic Gardens, Kew: London; Vol. 1.). The root bark of this plant is used locally as a traditional herbal remedy for a variety of ailments such as enlarged spleen, dysentery, helminthiasis, migraines, earaches, conjunctivitis and various other inflammatory conditions. In-depth studies have found that newbouldine has neurophysiological activity (Saburi, A.A.; Nia, R.; Fontaine, C.; Pays, M. Phytochemistry. 1993, 35, 1053-1055.). Newbouldine has two chiral ...

Claims

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Application Information

Patent Timeline
02 Jul 2019
Publication
CN109956948A
IPC
C07D487/04
CPC
C07D487/04
Inventors
俞斌勋; 仲萤