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Synthesis method of Corallidictyal D

A synthesis method and technology of skeleton compounds, which are applied in the fields of organic chemistry, bulk chemical production, organic chemistry, etc., can solve the problems of long reaction route, unsuitable for industrial production, low yield, etc. Fewer steps and better product selectivity

Active Publication Date: 2018-04-17
威海创惠环保科技有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] In 2013, Enrique Alvarez-Manzaneda et al achieved the synthesis of the natural product Corallidictyal D through an acid-selective catalytic ring-closing synthesis strategy in 10 steps (Cano M J, Bouanou H, Tapia R. Journal of organic chemistry, 2013, 78 (18): 9196-9204.), but the above methods all have disadvantages such as long reaction routes, low yields, and not suitable for industrial production

Method used

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  • Synthesis method of Corallidictyal D

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Effect test

Embodiment 1

[0020] Embodiment 1: the synthesis of sesquiterpene hydrazone (2, see accompanying drawing)

[0021] Dissolve 1 g (1, 4.5 mmol) of sesquiterpene aldehyde in 30 ml of anhydrous methanol, add 1.1 g (5.4 mmol) of p-toluenesulfonyl hydrazide, stir and react at room temperature for 5 hours, and TLC detects that the reaction is complete. After concentration, 1.6 g of white solid sesquiterpene sulfonylhydrazone was obtained with a yield of 95%.

Embodiment 2

[0022] Embodiment 2: the synthesis of skeleton compound (4 and 5, see accompanying drawing)

[0023] Dissolve 2.0 g (2, 5.1 mmol) of sesquiterpene sulfonylhydrazone in 250 ml of anhydrous tetrahydrofuran, add 490 mg (0.4 mmol) of tetrakistriphenylphosphine palladium, and 2.65 g (19.2 mmol) of potassium carbonate to repeatedly fill and exhaust argon Exhale three times to exhaust the air. Another 1.73 g (3, 4.2 mmol) of 1,2,4-trimethoxybenzene iodide was dissolved in 15 ml of anhydrous tetrahydrofuran, slowly added dropwise to the above reaction system, and the temperature was raised to 110 o C, the reaction was stirred for 10 hours, and the reaction was detected by TLC. Add 50 ml of water to the reaction system, extract with ethyl acetate (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 liquid 1.77 gram, the yield is 86%.

Embodiment 3

[0024] Embodiment 3: skeleton compound 4 is transformed into skeleton compound 5 (see accompanying drawing)

[0025] 1.16 g (2.58 mmol) of a mixture of skeleton compounds 4 and 5 was dissolved in 100 ml of ether, 0.1 g (0.78 mmol) of iodine was added to the above system, and stirred for 2 hours under sunlight. Add 100 ml of water to the reaction system, extract with ethyl acetate (20 mL x 3), combine the organic phases, wash with saturated brine, dry over anhydrous sodium sulfate, filter, and concentrate to obtain 1.15 g of a colorless oily liquid with a yield of 99%.

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Abstract

The invention relates to a synthesis method of marine natural product Corallidictyal D, and belongs to the field of chemical synthesis. The synthesis method comprises the following steps: taking sesquiterpene aldehyde 1 and 1-iodo-2,4,5-tri-alkoxybenzaldehydes 3 as starting materials, generating sesquiterpene hydrazine 2 from the sesquiterpene aldehyde 1 and p-toluenesulfonhydrazide, and couplingthe sesquiterpene hydrazine 2 with the 1-iodo-2,4,5-tri-alkoxybenzaldehydes under the catalysis of palladium to construct a skeleton 4 and a skeleton 5 of Siphonodictyal B; converting the skeleton compound 4 into the skeleton compound 5 under the effect of iodine, and removing a protecting group from the skeleton compound 5 under the effect of boron trichloride to generate Siphonodictyal B (6); and then generating Corallidictyal C (7) and Corallidictyal D (8) under the effect of acid. The synthesis method has the characteristics of less reaction steps, simplicity and convenience in operation,good selectivity of products, suitability for industrial production and the like.

Description

technical field [0001] The invention relates to a synthesis method of CorallidictyalD. Background technique [0002] The marine natural product Siphonodictyal B was first isolated and extracted from the deep-sea sponge Aka coralliphaga in 1981 (BS, P D, et al., Tetrahedron, 1981, 37: 979-982.), while the marine natural products Corallidictyal C and Corallidictyal D were isolated in 2007 It was isolated and extracted from the deep-sea sponge Aka coralliphaga in 2007, and exhibits protein kinase C inhibitory activity (Grube A, Assmann M, Lichte E. Journal of natural products, 2007, 70(4): 504-509.). [0003] There are few reports on the synthesis method of Siphonodictyal B, and the absolute configuration of this natural product was not fully determined until 2015, in which the methyl group at the C-8 position is in the α configuration. In 2015, Jonathan H. George et al. reported the synthesis of this compound, through the coupling of sesquiterpene aldehydes and aryl bromides,...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/94
CPCC07B2200/07C07D307/94Y02P20/55
Inventor 吴彦超王军利李惠静
Owner 威海创惠环保科技有限公司
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