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Synthetic method of marine terpenoid natural product namely ent-chromazonarol

A technology of natural products and synthetic methods, applied in the direction of organic chemistry, can solve the problems of long synthetic routes, expensive starting materials or reagents, etc., and achieve the effects of high total yield, few reaction steps, and good product selectivity

Active Publication Date: 2016-08-10
威海创惠环保科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] At present, the synthesis method of marine terpenoid natural product ent-chromazonarol has disadvantages such as long synthetic route, expensive starting materials or reaction reagents, etc.

Method used

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  • Synthetic method of marine terpenoid natural product namely ent-chromazonarol
  • Synthetic method of marine terpenoid natural product namely ent-chromazonarol

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Experimental program
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Embodiment 1

[0022] Embodiment 1: Sclare sulfonyl hydrazone (2, see attached figure 2 )Synthesis

[0023] Dissolve 2.38 g (1, 10.0 mmol) of sclarealdehyde in 30 ml of anhydrous methanol, add 1.86 g (10.0 mmol) of p-toluenesulfonyl hydrazide, stir and react at room temperature for 3 hours, and TLC detects that the reaction is complete. Concentrate to obtain white solid clarylar sulfonyl hydrazone.

Embodiment 2

[0024] Embodiment 2: enol compound (4, see appendix figure 2 )Synthesis

[0025] Dissolve 407 mg (2, 1.0 mmol) of clarylar sulfonylhydrazone in 4 ml of anhydrous tetrahydrofuran, add 23 mg (0.02 mmol) of tetrakistriphenylphosphine palladium, and 622 mg (4.5 mmol) of potassium carbonate to repeatedly fill and exhaust argon Exhale three times to exhaust the air. Another 264 mg (3, 1.0 mmol) of 2-iodo-1,4-dimethoxybenzene was dissolved in 2 ml of anhydrous tetrahydrofuran, slowly added dropwise to the above reaction system, heated to 110 °C, and stirred for 10 After 1 hour, TLC detected that the reaction was complete. Add 30 ml of water to the reaction system, extract with ethyl acetate (10 mL x 3), combine the organic phases, wash with saturated brine, dry over anhydrous sodium sulfate, filter, concentrate, and purify by column chromatography to give a light yellow oil 315 mg, the yield was 81%.

Embodiment 3

[0026] Embodiment 3: alkene terpene compound (5, see appendix figure 2 )Synthesis

[0027] Take 179 mg (4, 0.5 mmol) of enol compound and dissolve it in 2 ml of dry dichloromethane, add 174 mg (1.5 mmol) of triethylsilane and stir at 0 °C for 5 minutes, then add 114 mg (1.0 mmol) of trifluoroacetic acid dropwise. mmol) continued to react for 5 hours, and TLC detected that the reaction was complete. Add 10 ml of water, extract with ethyl acetate (10 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 146 mg of light yellow liquid with a yield of 85%. H NMR spectrum 1 H NMR (400 MHz, CDCl 3 ) d 6.78(d, 1H, J = 8.4 Hz), 6.69(d, 2H, J = 10.8Hz), 3.85(s, 3H), 3.79(s, 3H), 3.42(d, 1H, J = 17.8 Hz ), 3.26(d, 1H, J = 17.8Hz), 1.52(s, 3H), 1.05(s, 3H), 0.94(s, 3H), 0.88(s, 3H) ; C NMR 13 C NMR (100 MHz, CDCl 3 ) 153.4, 151.5, 137.2, 131.3, 129.0, 116.1, 110.2, 109.1...

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Abstract

The invention relates to a synthetic method of a marine terpenoid natural product namely ent-chromazonarol, and belongs to the field of chemical synthesis. The synthetic method provided by the invention uses salvia sclarea aldehyde and 2-iodo-1,4-dimethoxybenzene as starting materials. Salvia sclarea sulfonyl hydrazone is generated by a condensation reaction between salvia sclarea aldehyde and p-toluenesulfonyl hydrazide, an olefinic alcohol compound is obtained by a coupling reaction between salvia sclarea sulfonyl hydrazone and 2-iodo-1,4-dimethoxybenzene, an olefinic terpene compound is obtained by an intra-molecular reductive reaction and a double-bond isomerization reaction of the olefin alcohol compound, an olefinic phenol compound is obtained by an oxidation reaction and a reduction reaction of the olefinic terpene compound, and a target marine terpenoid natural product namely ent-chromazonarol is obtained by a cyclization reaction of the olefinic phenol compound. The synthetic method provided by the invention has the characteristics of few reaction steps, simple and convenient operation, good product selectivity, suitability of industrial production, and the like.

Description

technical field [0001] The invention relates to a synthesis method of marine terpene natural product ent-chromazonarol. Background technique [0002] Marine terpene natural product ent-chromazonarol (see attached figure 1 ) was first isolated from marine sponge dysidea pallescens in 1975 (Experientia, 1975, 31(10): 1117-1118). The backbone of this class of compounds consists of a sesquiterpene moiety and a quinone or hydroquinone moiety. This class of compounds exhibits various biological activities including anti-virus, anti-cancer, anti-fungal, anti-malarial, anti-tuberculosis and immune regulation (Science China Chemistry, 2013, 56(3): 349-353; Tetrahedron, 2000, 56 (7): 949-953; The Journal of Organic Chemistry, 1995, 60(22): 7290-7292; Journal of natural products, 1998, 61(12): 1502-1508). [0003] At present, the synthetic methods of ent-chromazonarol, a marine terpenoid natural product, have disadvantages such as long synthetic routes, expensive starting materials ...

Claims

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Application Information

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IPC IPC(8): C07D311/78
CPCC07D311/78
Inventor 吴彦超张振国李惠静戴春阳沈志仑
Owner 威海创惠环保科技有限公司
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