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Total synthetic method of Talienbisflavan A

A total synthesis and tea element technology, applied in the direction of organic chemistry, can solve the problem of no compound synthesis report, etc., and achieve the effect of less reaction steps, good product selectivity and high total yield

Active Publication Date: 2017-04-26
威海创惠环保科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

TalienbisflavanA is a new class of proanthocyanidin C8, 8-position dimer compound ( J. Agric. Food Chem. 2012, 60, 12170 −12176), there is no report on the synthesis of this compound

Method used

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  • Total synthetic method of Talienbisflavan A

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] Embodiment 1: the synthesis of dimeric catechin (2, see accompanying drawing)

[0018] O-Bz catechin (1, 1.0 mmol) and 5 mL of dioxane were added to the reaction flask, and formalin (35.0 uL) and 50% concentrated H were added at room temperature 2 SO 4 (0.5 mL), stirred at room temperature for 24 hours, and TLC detected the end of the reaction. Add 20 ml of water to quench, shake and separate the liquids, extract the aqueous phase with ethyl acetate (20 mL x 3), combine the organic phases, dry over anhydrous sodium sulfate, filter, concentrate, and purify by column chromatography to obtain dimer catechu Prime (2, see accompanying drawing), yield is 50%.

Embodiment 2

[0019] Example 2: Synthesis of dimeric epicatechin (3, see accompanying drawing)

[0020] Dimeric catechin (2, 0.5 mmol) and 5 ml of dichloromethane were added to the reaction flask, DMP (1.25 mmol) was added at room temperature, stirred at room temperature for 16 hours, and the reaction was detected by TLC. Add 5 ml of 10% sodium thiosulfate solution to quench, shake and separate the liquids, extract the aqueous phase with ethyl acetate (10 mL x 3), combine the organic phases, dry over anhydrous sodium sulfate, filter, concentrate, and purify by column chromatography , to obtain dimeric epicatechinone (3, see attached figure), with a yield of 87%.

Embodiment 3

[0021] Example 3: Synthesis of dimeric epicatechin (4, see accompanying drawing)

[0022] Add dimeric epicatechin (3, 0.5 mmol) and 5 ml THF into the reaction flask, cool to -78°C, slowly add L-Selectride (1 mmol) dropwise at this temperature, stir at -78°C for 4 hours , TLC detects that the reaction is complete. Add 5 ml of water to quench, shake and separate the liquids, extract the aqueous phase with ethyl acetate (10 mL x 3), combine the organic phases, dry over anhydrous sodium sulfate, filter, concentrate, and purify by column chromatography to obtain dimerized form Tea element (4, see accompanying drawing), yield is 75%.

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Abstract

The invention relates to a total synthetic method of the proanthocyanidin natural product Talienbisflavan A and belongs to the field of chemical synthesis. The natural product Talienbisflavan A (see figures) is synthesized by: synthesizing dimeric catechin via acid catalyzed dimerization of formaldehyde, subjecting the dimeric catechin to DMP (Dess-Martin periodinane) oxidation and L-Selectride selective reduction to synthesize dimeric epicatechin, subjecting the dimeric epicatechin to coupling reaction with benzyl-protected gallic acid to synthesize dimeric epicatechin gallate, subjecting the dimeric epicatechin gallate to palladium / carbon debenzylation. The method of the invention has the advantages that reaction steps are few, total yield is high, product selectivity is good, and the method is suitable for industrial production.

Description

technical field [0001] The invention relates to a total synthesis method of TalienbisflavanA. Background technique [0002] Proanthocyanidins are one of the components of plant pigments and are a class of secondary metabolites of polyphenols widely present in various plants. Studies have found that proanthocyanidins natural products have a variety of biological activities, and have various physiological functions such as antioxidant, antibacterial, antimutagenic, and antihypertensive ( Curr. Med. Chem . 2010, 17, 1756). In recent years, studies have shown that procyanidins natural products have important application value in marine antifouling. Structurally, proanthocyanidins are composed of different amounts of catechin or epicatechin. Studies have found that proanthocyanidin C8, an 8-position dimer compound, has excellent antioxidant and free radical scavenging capabilities ( Pharm. Biol. 2010, 48, 116), there are few reports on the synthesis of such skeleton compound...

Claims

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Application Information

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IPC IPC(8): C07D311/62
CPCC07D311/62
Inventor 李惠静黄登明吴彦超
Owner 威海创惠环保科技有限公司
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