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Total synthesis method of strigolactones GR24

A technology of strigolactone and GR24 is applied in the field of synthesizing a class of plant hormone strigolactones, which can solve the problems of lengthy synthesis methods, high toxicity or harsh operating conditions, and achieves high product purity, simple reaction conditions, The effect of cheap and easily available raw materials

Inactive Publication Date: 2013-11-20
NANJING AGRICULTURAL UNIVERSITY
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Problems solved by technology

It is worth noting that the above two synthetic methods are relatively lengthy, and the reagents used are either highly toxic or the operating conditions are harsh (strict anhydrous operation)

Method used

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  • Total synthesis method of strigolactones GR24
  • Total synthesis method of strigolactones GR24

Examples

Experimental program
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Embodiment

[0037] Example: Preparation of strigolactone GR24 with 1-indanone as raw material

[0038] Synthesis of compound B: Add 1-indanone A (13.2 g, 0.1 mol), glyoxylic acid (17.5 g, 0.24 mol), tetrahydrofuran (20 ml) and concentrated hydrochloric acid (0.5 ml , 37%), heated to reflux for 1.5 hours, cooled to room temperature, added a large amount of cold water (200 mL) to precipitate the product, and obtained 18.63 g of light yellow solid Compound B, yield: 99%;

[0039] Synthesis of compound C: Add compound B (6.27 g, 0.033 mol), zinc powder (2.6 g, 0.04 mol), acetic acid (50 ml) and water (15 ml) into a single-necked flask (200 ml), and heat to reflux for 5 hours , after cooling to room temperature, the zinc powder was filtered off, the reaction solution was extracted with ethyl acetate, the organic phase was separated, and the organic phase was dried over anhydrous sodium sulfate, and concentrated to obtain 5.58 g of light yellow solid product Compound C, with a yield of 89%;

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Abstract

The invention discloses a novel total synthesis method of strigolactones GR24 which is a plant hormone. The total synthesis method of the strigolactones GR24 comprises the following steps of: carrying out condensation, reduction, lactonization and condensation salt forming reaction on 1-indanone to synthesize a compound F; carrying out dehydrogenation reaction and bromination on 2-methyl butyrolactone to synthesize a compound H; and finally carrying out a substitution reaction on the compound F and the compound H to obtain the strigolactones GR24. According to the total synthesis method, raw materials are low in cost and easily available, the operation is simple and feasible, no strict water-free and oxygen-free operation is required, all steps are simple and feasible except the last step which needs column chromatography isolation, and the whole synthesis route is very suitable for large-scale production. Furthermore, the total synthesis method can be universally used for synthesis of various strigolactones derivatives.

Description

technical field [0001] The invention belongs to the technical field of synthesizing a kind of plant hormone strigolactone, and in particular relates to a total synthesis method of strigolactone GR24. Background technique [0002] Strigolactone is a general term for some natural strigolactones and their synthetic analogues or derivatives. The earliest strigolactone is Strigol, which was isolated by Crook in 1966 from the rhizosphere exudates of the non-host plant cotton of Striga, which can induce the growth of plants such as Striga and Liedang. The seeds germinated and were later found in other plants such as corn, sorghum, and millet. The artificially synthesized strigol analogs were reported by Johnson et al. in 1976, and there are GR (germination releaser) series such as GR24, GR7, GR3, etc. Among them, GR24 has the highest activity, and it is also the most strigolactone-like compound used by scientific researchers at home and abroad. It can be used as a new type of pla...

Claims

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Application Information

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IPC IPC(8): C07D307/93
Inventor 吴磊许俊旭查满荣丁艳锋
Owner NANJING AGRICULTURAL UNIVERSITY
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