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Laingolide A and diastereoisomer and synthetic method thereof

A technology of diastereomers and synthesis methods, applied in the field of LaingolideA and its diastereomers, can solve the problem of lack of synthesis methods, and achieve the effects of clear route, great practical value and significance, and high synthesis efficiency

Active Publication Date: 2020-11-17
PEKING UNIV SHENZHEN GRADUATE SCHOOL +1
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] The purpose of this application is to provide a synthetic method of Laingolide A and its diastereoisomers, and a kind of Laingolide A and its diastereoisomers, aiming to solve the existing Laingolide A and its diastereoisomers to a certain extent. Enantiomers can only be extracted from seaweed without the technical problems of synthetic methods

Method used

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  • Laingolide A and diastereoisomer and synthetic method thereof
  • Laingolide A and diastereoisomer and synthetic method thereof
  • Laingolide A and diastereoisomer and synthetic method thereof

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preparation example Construction

[0024] The first aspect of the embodiment of the present application provides a synthetic method of Laingolide A and its diastereoisomers, comprising steps:

[0025] S10. Obtain compound 8 or ent-8; obtain compound 15 or 18;

[0026] S20. Compound 8 or ent-8 and compound 15 or 18 are subjected to a Julia olefin synthesis reaction to obtain compound A;

[0027] S30. Reductive hydrogenation treatment is performed on compound A to obtain compound B;

[0028] S40. Oxidizing compound B to obtain compound C;

[0029] S50. performing an esterification reaction after compound C is assembled with an amide bond to obtain compound D;

[0030] S60. After compound D is subjected to olefin metathesis reaction, olefin isomerization reaction is carried out to obtain Laingolide A or the diastereoisomers of Laingolide A;

[0031] Wherein, the structural formula of compound 8 is: The structural formula of compound ent-8 is: The structural formula of compound 15 is: The structural formul...

Embodiment 1

[0090] Embodiment 1: synthetic compound 8 intermediate, design following synthetic route:

[0091]

[0092] Include the following specific steps:

[0093] 1. Synthesis of compound 35: (R)-Roche ester (1.0g, 8.5mmol, 1.0eq.), imidazole (1.2 g, 16.9mmol, 2.0eq.) and 4-dimethylaminopyridine DMAP (207.0 mg, 1.7mmol, 0.2eq.) was dissolved in dry dichloromethane DCM (40mL, 0.21M). At 0 °C, tert-butyldimethylsilyl chloride TBSCl (1.5 g, 10.2 mmol, 1.2 eq.) was added, then the reaction temperature of the reaction was raised to room temperature and stirring was continued for 16 h. After the reaction is complete, add saturated NH 4 The reaction was quenched with Cl (30 mL), then the aqueous phase was extracted with DCM (3×40 mL), the organic phases were combined and washed with excess anhydrous Na 2 SO 4 Drying, followed by filtration to obtain the filtrate containing the product, the filtrate was concentrated by a vacuum water pump to obtain a crude product, and finally the obta...

Embodiment 2

[0097] Embodiment 2: synthetic compound ent-8 intermediate, design following synthetic route:

[0098]

[0099] Include the following specific steps:

[0100] 1. Synthesis of compound ent-35: (S)-Roche ester (1.0g, 8.5mmol, 1.0eq.), imidazole (1.2g, 16.9mmol, 2.0eq.) and DMAP (207.0mg, 1.7mmol, 0.2 eq.) was dissolved in dry DCM (40mL, 0.21M), and TBSCl (1.5g, 10.2mmol, 1.2eq.) was added at 0°C, then the reaction temperature was raised to room temperature and stirring was continued for 16h. After the reaction is complete, add saturated NH 4 The reaction was quenched with Cl (30 mL), then the aqueous phase was extracted with DCM (3×40 mL), the organic phases were combined and washed with excess anhydrous Na 2 SO 4 Drying, followed by filtration to obtain a filtrate containing the product, the filtrate was concentrated by a vacuum water pump to obtain a crude product, and finally the obtained crude product was purified by column chromatography to obtain compound ent-35 (1.8...

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Abstract

The invention belongs to the technical field of synthesis, and particularly relates to a synthesis method of Laingolide A and a diastereoisomer thereof, which comprises the following steps: preparinga compound 8 or ent-8; preparing a compound 15 or 18; carrying out Julia olefination reaction on the compound 8 or ent-8 and a compound 15 or 18 to obtain a compound A; carrying out reductive hydrogenation treatment on the compound A to obtain a compound B; carrying out oxidation treatment on the compound B to obtain a compound C; carrying out amido bond assembly on the compound C and then carrying out esterification reaction to obtain a compound D; and carrying out olefin metathesis reaction on the compound D, and then carrying out olefin isomerization reaction to obtain the Laingolide A or the diastereoisomer thereof. The synthesis method provided by the embodiment of the invention is clear in route and high in synthesis efficiency, and is beneficial to the research on the biological activity of the Laingolide A and the diastereoisomer.

Description

technical field [0001] The application belongs to the technical field of synthesis, and in particular relates to a synthetic method of Laingolide A and its diastereoisomers, and a kind of Laingolide A and its diastereoisomers. Background technique [0002] Laingolide A was isolated from the blue-green Lyngbyabouillonii seaweed on Laine Island by D. Daloze's research group in 1996. The molecule has a non-conjugated N-methyl-trans-alkenyl amide bond in the structure. In 2010, another molecule of the Laingolide family, Laingolide B, was isolated from the cyanobacterium Lyngbya bouillonii in Apra Harbor Shoal Reef, Guam by Hendrik Luesch's group. In the same year, Palmyrolide A, which also has a structural unit of non-conjugated N-methyl-trans-alkenyl amide bonds in the ring, was obtained from the mixed marine cyanobacteria of the Palmyra Atoll in the North Pacific by the Gerwick research group (Leptolyngbya cf. and Oscillatoria spp.) isolated from. Since their isolation and r...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D267/00
CPCC07D267/00C07B2200/07Y02P20/55
Inventor 叶涛郭益安吴福松张涛
Owner PEKING UNIV SHENZHEN GRADUATE SCHOOL
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