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Method for synthesizing marine natural product Aureol

A technology of natural products and synthetic methods, applied in the direction of organic chemistry, organic chemistry, etc., can solve the problems of long reaction route, low yield, unsuitable for industrial production, etc., achieve high total yield, good product selectivity, and reaction The effect of fewer steps

Active Publication Date: 2018-04-24
HARBIN INST OF TECH AT WEIHAI
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the above-mentioned methods all have disadvantages such as long reaction route and low yield, and are not suitable for industrialized production.

Method used

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  • Method for synthesizing marine natural product Aureol

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0015] Embodiment 1: the synthesis of rearrangement iodide (4, see accompanying drawing)

[0016] Dissolve 1 g (3, 2.6 mmol) of (+) Sclareus iodide in 30 ml of anhydrous dichloromethane, add 0.75 ml (5.3 mmol) of boron trifluoride ether at -40 °C, and stir for 30 minutes , TLC detects that the reaction is complete. Add 50 ml of water to the reaction system, extract with dichloromethane (30 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 oily substance 0.53 Gram, the yield is 63%.

Embodiment 2

[0017] Embodiment 2: the synthesis of skeleton compound (6, see accompanying drawing)

[0018] Dissolve 0.5 g (4, 1.5 mmol) of the rearranged iodide in 25 ml of anhydrous tetrahydrofuran, and add 220 mg (0.6 mmol) of (1,1'-bis(diphenylphosphino)ferrocene)nickel dichloride , repeatedly filling and exhausting argon gas three times, exhausting the air. Another 25 ml (5, 15 mmol) of 1-iodo-2,5-dimethoxyphenyl Grignard reagent was slowly added dropwise to the above reaction system, and the temperature was raised to 68 o C, the reaction was stirred for 36 hours, and the reaction was detected by TLC. At room temperature, add 50 ml of water to the reaction system, extract with ethyl acetate (30 mL x3), combine the organic phases, wash with saturated brine, dry over anhydrous sodium sulfate, filter, concentrate, and purify by column chromatography to obtain a colorless oil 0.57 g of liquid, the yield is 56%.

[0019] The present invention relates to the reaction of (+) Sclareus iodi...

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Abstract

The invention relates to a method for synthesizing a marine natural product Aureol, and belongs to the field of chemical synthesis. Iodo substances 3 and 1-iodine-2, 5-di-alkoxy Grignard reagents 5 are used as starting materials, and the iodo substances 3 are generated from (+) sclareolide. The method includes generating rearrangement iodo substances 4 from the salvia sclarea iodo substances 3 andboron trifluoride diethyl ether; coupling the rearrangement iodo substances 4 and the 1-iodine-2, 5-di-alkoxy Grignard reagents 5 under the catalytic effects of nickel to construct key synthesis precursor frameworks 6 for the Aureol; carrying out known 2-step reaction on framework compounds 6 to obtain the marine natural product Aureol. The method has the advantages that the method includes few reaction steps, is easy and convenient to operate, good in product selectivity and suitable for industrial production, and the like.

Description

technical field [0001] The invention relates to a method for synthesizing marine natural product Aureol. Background technique [0002] Aureol, a marine natural product, was developed from a deep-sea sponge in 1980 Smenospongia aurea It was isolated and extracted for the first time in (Djura P, Stierle D B, Sullivan B, Faulkner D J, Arnold E V, Clardy J., The Journal of organic chemistry, 1980, 45: 1435-1441.). This substance has selective antitumor activity (Longley R E, McConnell O J, Essich E, Harmody D, Journal of natural products, 1993, 56: 915-920.). [0003] The synthetic method about Aureol has been reported, and Tadashi Katoh et al. reported in 2003 that (+)-5-methyl-Wieland-Miescher ketone was used as a substrate to complete the synthetic research of Aureol through 22 steps (Nakamura M, Suzuki A, Nakatani M, Fuchikami T, Inoue M, Katoh T. Tetrahedron Letters, 2002, 43:6929-6932.). George et al completed the synthesis of Aureol in 2012 using (+)-sclerene as a subs...

Claims

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Application Information

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IPC IPC(8): C07D311/96
CPCC07B2200/07C07D311/96
Inventor 吴彦超王军利李惠静
Owner HARBIN INST OF TECH AT WEIHAI
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