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Synthetic method for ocean natural product Haterumadienone

A technology of natural products and synthetic methods, applied in the production of bulk chemicals, organic chemistry, etc., to achieve the effects of high total yield, fewer reaction steps, and good product selectivity

Active Publication Date: 2016-05-04
HARBIN INST OF TECH AT WEIHAI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, so far there is no report on the synthesis of the marine natural product Haterumadienone

Method used

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  • Synthetic method for ocean natural product Haterumadienone
  • Synthetic method for ocean natural product Haterumadienone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] Embodiment 1: Cyclopentanedione (3, see attached figure 2 )Synthesis

[0019] Dissolve 0.98 g (2, 10.0 mmol) of cyclopentanedione in 25 ml of absolute ethanol, add hydrochloric acid (1 mmol), stir and react at room temperature for 3 hours, and TLC detects that the reaction is complete. Add 30 ml of water, extract with dichloromethane (30mLx3), combine the organic phases, wash with saturated sodium bicarbonate solution, dry over anhydrous sodium sulfate, filter, concentrate, and purify by column chromatography to obtain a light yellow oily substance ethoxy-protected ring Pentanedione 1.07 grams, yield is 85%.

Embodiment 2

[0020] Embodiment 2: beta-hydroxycyclopentanone (5, see attached figure 2 )Synthesis

[0021] Dissolve 126 mg (3, 1.0 mmol) of ethoxy-protected cyclopentanedione in 2 ml of anhydrous tetrahydrofuran, repeatedly fill and exhaust argon three times, exhaust the air, and cool down to -78 o c. LDA (3 mmol) was added and the reaction was kept stirring at this temperature for 30 minutes. Another 238 mg (-) sclarealdehyde (4, 1.0 mmol) was dissolved in 1 ml of anhydrous tetrahydrofuran, and slowly added dropwise to the above reaction system, and the stirring reaction was continued for 12 hours, and the reaction was detected by TLC. 5 ml of saturated ammonium chloride solution was added dropwise to the reaction system to quench the reaction, and stirring was continued at room temperature for 30 minutes. Extract with ethyl acetate (10mLx3), combine the organic phases, wash with saturated brine, dry over anhydrous sodium sulfate, filter, concentrate, and purify by column chromatograp...

Embodiment 3

[0022] Embodiment 3: Haterumadienone (1, see attached figure 2 )Synthesis

[0023] Dissolve 182 mg (5,0.5 mmol) of beta-hydroxycyclopentanone of dicyclic sesquiterpene in 2 ml of benzene, add p-toluenesulfonic acid (0.5 mmol), stir and react at room temperature for 3 hours, and TLC detects that the reaction is complete. Add 10 ml of ethyl acetate, wash with saturated brine (10 mL x 3), dry the organic phase over anhydrous sodium sulfate, filter, concentrate, and purify by column chromatography to obtain 105 mg of a light yellow solid with a yield of 70%. Optical rotation [α] D 25 -73.6°(c=0.15, CHCl 3 ); H NMR spectrum 1 HNMR (400MHz, C 6 D. 6 )σ5.61(s,1H),5.28(d,1H),2.83(d,1H),2.75(d,1H),1.96(td,1H),1.36(m,1H),1.31(m,2H ),1.26(m,1H),1.25(m,2H),1.03(dt,1H),0.95(s,3H),0.80(s,3H),0.74(s,3H),0.5(s,3H) ,0.67(dt,1H),0.67(dd,1H); C NMR 13 CNMR (75MHz, C 6 D. 6 )σ199.2, 177.9, 132.9, 121.2, 110.1, 80.1, 53.8, 53.7, 41.8, 39.8, 39.4, 39.4, 37.8, 33.6, 33.1, 28.5, 22.0, 18....

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Abstract

The invention relates to a synthetic method for an ocean natural product Haterumadienone and belongs to the field of chemical synthesis. The synthetic method comprises the steps that (-) aromatic perilla aldehyde and dinone serve as staring materials, bicycle-sesquiterpenes beta-hydroxyl cyclopentanone is prepared through an aldol reaction of dinone protected through (-) aromatic perilla aldehyde and alkyl, and thus a hate Haterumadienone framework is structured; a cyclization-elimination reaction is carried out through a nucleophilic reaction by attacking hydroxyl with acid-catalyzed hydroxyl, and finally the ocean natural product Haterumadienone is synthesized. The synthetic method has the advantages that few reaction steps are needed, operation is easy and convenient, product selectivity is good, and the synthetic method is suitable for industrial production.

Description

technical field [0001] The invention relates to a synthetic method of marine natural product Haterumadienone. Background technique [0002] The marine natural product Haterumadienone belongs to the new Puupehenone class of natural products (see attached figure 1 ). Puupehenone was isolated and extracted from Hawaiian sponge in 1979. Its derivatives are important marine metabolites that exhibit various biological activities including cytotoxicity, anti-virus, anti-cancer, anti-fungal, anti-malarial, anti-tuberculosis and immune regulation. (Pure and Applied Chemistry, 1979, 51 (9): 1893-1900; The Journal of Organic Chemistry, 1995, 60 (22): 7290-7292; Journal of Natural Products, 1998, 61 (12): 1502-1508). The structure of the derivatives involved in this patent is quite different from that of Puupehenone. In addition to having a common sesquiterpene moiety and an oxygen-containing six-membered pyran heterocycle, the head end of Puupehenone is a conjugated six-membered unsa...

Claims

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Application Information

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IPC IPC(8): C07D311/94C07D311/78
CPCC07D311/78C07D311/94Y02P20/55
Inventor 王洪双李惠静吴彦超周培林张振国
Owner HARBIN INST OF TECH AT WEIHAI
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