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Novel method for synthesizing natural product Cyanolide A analogue

A technology of natural products and analogues, applied in chemical instruments and methods, sugar derivatives, sugar derivatives, etc., can solve the problems of high synthesis cost and low yield, achieve simple operation, reduce production cost, and increase yield Effect

Inactive Publication Date: 2017-09-05
JIANGXI SCI & TECH NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The purpose of the present invention is to overcome the problems of expensive synthetic cost and low yield in the existing synthetic methods, and provides a new synthetic method of natural product Cyanolide A analogues

Method used

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  • Novel method for synthesizing natural product Cyanolide A analogue
  • Novel method for synthesizing natural product Cyanolide A analogue
  • Novel method for synthesizing natural product Cyanolide A analogue

Examples

Experimental program
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Effect test

Embodiment 1

[0020] Embodiment 1: the synthesis of formula 3 compound

[0021] Under the protection of nitrogen, the chiral auxiliary formula 2 (1.19g, 4.75mmol) was dissolved in 31ml of dry dichloromethane, and then the reaction system was placed in an ice-water mixture and cooled to 0°C, and 1.04ml of tetrachloride was slowly added dropwise. Titanium chloride. Stir at 0°C for 5 minutes, dissolve 1.65ml of DIPEA (diisopropylethylamine) in 3ml of dry dichloromethane and add to the reaction system. Then the reaction system was moved to -78°C. After reacting for 30 minutes, a solution of propionaldehyde formula 1 (1ml, 14.25mmol) in dry dichloromethane (9ml) was added dropwise, and the reaction system continued to react at -78°C for 3h. . After TLC (thin layer chromatography) detection reaction is complete, with saturated NH 4 After the Cl solution was quenched, the reaction system was moved to room temperature. After the solution temperature rose to room temperature, it was extracted wit...

Embodiment 2

[0022] Embodiment 2: the synthesis of formula 4 compound

[0023] Under the protection of nitrogen, the raw material formula 3 (2.8297g, 9.14mmol) was dissolved in 36.56ml of dry tetrahydrofuran, the reaction system was placed in an ice-water mixture and cooled to 0°C, and then monomethyl malonate potassium salt ( 2.85g, 18.28mmol), imidazole (1.24g, 18.28mmol) and anhydrous magnesium chloride (1.74g, 18.28mmol), the reaction system was reacted at room temperature for 44h, and saturated NH 4 The Cl solution was quenched, extracted with ethyl acetate, the organic phases were combined, dried with anhydrous sodium sulfate, filtered, and distilled under reduced pressure to obtain the crude product, which was separated and purified by silica gel column chromatography to obtain 1.2106 g of the compound of formula 4 in a yellow viscous shape. rate 76%; 1 H NMR (400MHz, CDCl 3 ):δ3.99(s,1H),3.72(s,3H),3.48(s,2H),2.78-2.75(m,1H),2.74-2.59(m,2H),1.57-1.40(m,2H ),0.93(t,J=7.4Hz,3H); ...

Embodiment 3

[0024] Embodiment 3: the synthesis of formula 5 compounds

[0025] Under the protection of nitrogen, the raw material formula 4 (414.4mg, 2.38mmol) was dissolved in 14ml of dry tetrahydrofuran, the reaction system was placed in an ice-water mixture and cooled to 0°C, and then 7.14ml of triethylboron was added dropwise. After ethyl boron was added dropwise, 7.2ml of refined methanol was added dropwise, and the reaction was continued for 1h. Then the reaction system was moved to -78°C, and 269.99 mg of NaBH was added 4 , stirred at this temperature for 1 hour, and TLC detected that the reaction was completely completed. with saturated NH 4 The Cl solution was quenched, extracted with ethyl acetate, the organic phases were combined, dried over anhydrous sodium sulfate, filtered, and distilled under reduced pressure to obtain a crude product. Then add 15ml of ethyl acetate to dissolve, add 20mL of 3% hydrogen peroxide solution dropwise, after TLC detects that the reaction is co...

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Abstract

The invention discloses a novel method for synthesizing natural product Cyanolide A analogue. The method includes: using propionaldehyde 1 and Evans chiral auxiliary 2 as starting raw materials, and synthesizing a segment 9 through Evans Aldol, potassium methyl malonate condition, Bet3/NaBH4 reduction, p-anisaldehyde dimethyl acetal protection, DIBAL-H reduction and Mukaiyama Aldol; synthesizing a segment 11 through MOMCl protection and p-anisaldehyde dimethyl acetal protection removal, and building a tetrahydropyran ring with potassium carbonate to obtain a compound 12; subjecting the compound 12 to hydrolysis, Yamaguchi reaction and MOM protection removal to synthesize a segment 15, subjecting the segment 15 and a compound 16 to glycosylation to obtain a product cyanolide A analogue. A key step is Mukaiyama aldol reaction catalyzed by Ti(O-i-Pr)2Cl2, product yield is high, and three-dimensional selectivity control is good.

Description

technical field [0001] The present invention relates to a new method for the stereoselective synthesis of natural product Cyanolide A analogues, in detail, propionaldehyde 1 and Evans auxiliary agent 2 are used as starting materials, and Ti(O-i-Pr) 2 Cl 2 The catalyzed Mukaiyama aldol reaction is a new method for the synthesis of natural product Cyanolide A analogs through a series of reactions including the construction of hydroxyl chirality as the key step. Background technique [0002] Cyanolide A is a natural product with molluscicidal activity extracted by Gerwick's group in 2010 from a species of Lindella in Papua New Guinea. Cyanolide A is a dimeric glycoside macrolide with a C 2 The structure of the axis of symmetry, a 16-membered macrolide in the center is fused with two tetrahydropyran rings and two xylose-type substrates. Since the molluscicidal activity of Cyanolide A plays a key role in human health and has great potential as an effective and selective mollus...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H17/08C07H1/00
CPCC07H1/00C07H17/08
Inventor 黄双平王博冷晓李晓彤徐天祥梁程王晓季
Owner JIANGXI SCI & TECH NORMAL UNIV
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