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Synthetic method of austrodoral and austrodoric acid

A compound and natural product technology, applied in the direction of chemical instruments and methods, carbon-based compound preparation, organic compound preparation, etc., can solve the problems of expensive starting materials or reaction reagents, cumbersome experimental operations, long synthetic routes, etc., and achieve easy Implementation, easy reaction conditions, ideal yield

Active Publication Date: 2016-06-15
HARBIN INST OF TECH AT WEIHAI
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] At present, there are few reports on the synthetic methods of marine terpenoid natural products austrodoral and austrodoric acid, and most of them have disadvantages such as long synthetic routes, expensive starting materials or reagents, low yields, and cumbersome experimental operations.

Method used

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  • Synthetic method of austrodoral and austrodoric acid

Examples

Experimental program
Comparison scheme
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Embodiment 1

[0019] Embodiment 1: sesquiterpene o-diol compound ( 2 , see Figure) synthesis.

[0020] at -78 o Under C, first 444 mg of sesquiterpene alcohol compound ( 1 , see attached picture, 2.0mmol) was dissolved in 10mL of dichloromethane, and ozone was passed into the reaction system until it turned blue; then N was passed into it 2 Exhaust the ozone remaining in the reaction system from the reaction system; finally add NaBH to the reaction system 4 (6.0mmol), slowly warmed up to room temperature, stirred for 2-3 hours; TLC detected the end of the reaction, added 5mL dilute hydrochloric acid to quench the reaction, the reaction solution was extracted with dichloromethane (15mLx3), combined organic phase, dried over anhydrous sodium sulfate, It was filtered, concentrated, and purified by column chromatography to obtain 452 mg of white solid with a yield of 100%.

Embodiment 2

[0021] Example 2: Synthesis of marine terpenoid natural product austrodoral (see attached figure).

[0022] Get 226mg sesquiterpene o-diol compound ( 2 , 1.0mmol) was dissolved in 5mL dichloromethane, added 0.1mmol boron trifluoride diethyl ether, stirred and reacted at room temperature for 12 hours, TLC detected the end of the reaction, added 10mL saturated ammonium chloride solution to quench the reaction, and the reaction solution was dichloromethane Extract (15mLx3), combine the organic phases, dry over anhydrous sodium sulfate, filter, concentrate, and purify by column chromatography to obtain austrodoral 177mg as a colorless oil with a yield of 85%. H NMR spectrum 1 H-NMR (400MHz, CDCl 3 )δ:0.83(3H,s),0.85(3H,s),0.86(3H,s),0.94(1H,ddd, J =4.0,13.0,13.0Hz),1.01(3H,s),1.16(1H,dt, J =4.0,13.0Hz),1.22(1H,dd, J =7.5,12.5Hz),1.27(1H,ddd, J =2.5,11.0,13.0Hz),1.33–1.51(3H,m),1.52–1.70(3H,m),2.13(1H,ddd, J =6.0,9.5,13.0Hz),9.65(1H,s).0.98(d,3H, J =6.4Hz), 0.93(s,3H), 0.88...

Embodiment 3

[0023] Embodiment 3: Terrestrial terpene natural product 8- epi - Synthesis of 11-nordriman-9-one (see attached picture).

[0024] Get 226mg sesquiterpene o-diol compound ( 2 , see attached picture, 1.0 mmol) was dissolved in 5 mL of dichloromethane, 2.0 mmol of boron trifluoride ether was added, stirred and reacted at room temperature for 2 hours, and the reaction was detected by TLC. Add 10 mL of saturated ammonium chloride solution to quench the reaction, extract the reaction liquid with dichloromethane (15 mL x 3), combine the organic phases, wash with saturated brine, dry over anhydrous sodium sulfate, filter, concentrate, and purify by column chromatography to obtain a colorless solid 8-epi-11-nordriman-9-one198mg, the yield is 95%. H NMR spectrum 1 HNMR (400MHz, CDCl 3 )2.68(m,1H),2.10(ddd,1H, J =3.2Hz, J =6.3Hz, J =14.0Hz),1.72(m,1H),1.57(m,4H),1.40(d,1H, J =13.5Hz),1.23(m,3H),1.14(s,3H),1.09(m,1H),0.98(d,3H, J =6.4Hz), 0.93(s,3H), 0.88(s,3H); C NMR 13 CNMR ...

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Abstract

The invention relates to a synthetic method of an ocean terpene natural product austrodoral, austordoric acid and a land terpene natural product 8-epi-11-nordriman-9-one and belongs to the field of chemical synthesis. Sesquiterpenes vicinal diol is prepared by selective ozonization reaction of sesquiterpenes enol, the land terpene natural product 8-epi-11-nordriman-9-one and the ocean terpene natural product austrodoral are synthesized by the selective rearrangement reaction of the sesquiterpenes vicinal diol, and the ocean terpene natural product austrodoric acid is synthesized by oxidation reaction of the austrodoral. The method has the characteristics of low production cost, simple process conditions, easiness in control, suitability for industrial production, high overall yield and the like.

Description

technical field [0001] The present invention relates to a synthetic method of austrodoral and austrodoricacid. Background technique [0002] The marine terpene natural products austrodoral and austrodoricacid (see attached image) were recovered from Terra Nova Bay, Antarctica in 2003 A. kerguelenensis The metabolites isolated and extracted from have a new carbon skeleton ( Tetrahedron letters, 2003, 44, 1495 – 1498 ). The marine terpene natural products austrodoral and austrodoricacid belong to the austrodorane class of natural products, which have antifungal, antimicrobial, antifeedant and antitumor activities ( Tetrahedron, 2007, 63, 11943 – 11951 ). Marine terpene natural products austrodoral and austrodoricacid are rare in marine organisms and difficult to separate. It is particularly necessary to explore a suitable synthesis method, which is conducive to further research on their biological characteristics. [0003] At present, there are few reports on the synth...

Claims

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Application Information

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IPC IPC(8): C07C61/13C07C51/16C07C47/347C07C45/52C07C49/447
CPCC07C29/50C07C45/52C07C51/16C07C61/13C07C47/347C07C49/447C07C35/36
Inventor 王军利吴彦超李超逸王龙飞张振国戴春阳沈至仑李惠静
Owner HARBIN INST OF TECH AT WEIHAI
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