New composite method for triptolide

A technology for triptolide and a synthesis method, which is applied in the field of organic compound synthesis, can solve the problems of inability to synthesize a large number of target compounds, poor selectivity of asymmetric reaction, low yield of multi-step reaction, etc. The effect of technologicalization, short route and convenient operation

Active Publication Date: 2010-02-03
SHANGHAI HAOYUAN CHEMEXPRESS
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although this method provides the first asymmetric total synthesis of the target compound, the multi-step reaction yield is still very low, the operation is difficult, and the key asymm

Method used

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  • New composite method for triptolide
  • New composite method for triptolide
  • New composite method for triptolide

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Embodiment 1

[0030] An embodiment of the present invention is provided below, wherein R 1 is methyl, R 2 For trimethylsilyl. The reaction of 4 and 5 was carried out in p-trifluoromethylbenzyl cinchonin bromide (formula 7) and sodium hydroxide, compound 9 was enol etherified with sodium hydride and trimethylchlorosilane and then reduced under Pd-C catalysis Compound 10 was obtained. Compound 14 was treated with sulfuric acid / isopropanol to give compound 3.

[0031] Formula 7

[0032] Ketone 4 (7.98g, 42mmol) iodide 5 (30g, 126mmol) and catalyst A (2.2g, 4.2mmol) were mixed and dissolved in toluene. 50% NaOH aqueous solution (6 mL) was added dropwise to the above solution with stirring at 0°C. After the dropwise addition, the reaction was slowly raised to room temperature and stirred for 48h. The organic layer was separated and the aqueous phase was extracted with ether. The organic phases were combined, the solvent was evaporated, and the residue was subjected to silica gel column ...

Embodiment 2

[0043] Specific embodiments of the present invention are provided below, wherein R 1 is ethyl, R 2 For triethylsilyl. The reaction of 4 and 5 is carried out in p-trifluoromethylbenzylquinine bromide (catalyst B) and sodium hydroxide, compound 9 is enol etherified with sodium hydride and triethylchlorosilane under Raney-Ni catalysis Reduction affords compound 10. Compound 14 was treated with methanesulfonic acid / isopropanol to give compound 3.

[0044] Ketone 4 (7.98 g, 42 mmol), iodide 5 (30 g, 126 mmol) and catalyst B (2.2 g, 4.2 mmol) were mixed and dissolved in toluene. 50% NaOH aqueous solution (6 mL) was added dropwise to the above solution with stirring at 0°C. After the dropwise addition, the reaction was slowly raised to room temperature and stirred for 48h. The organic layer was separated and the aqueous phase was extracted with ether. The organic phases were combined, the solvent was evaporated, and the residue was subjected to silica gel column chromatography ...

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Abstract

The invention provides a new and effective method for asymmetrically compositing triptolide, belonging to the chemical composite field. The method takes 5-methoxyl-2-tetralone and 2-(2-iodine ethyl)-1, 4-butyrolactone as initial materials and composites the triptolide by chiral induction. The method is brief and convenient in operation and has high yield. As the reaction condition is mild, the composite method is easily industrialized and is further used for large-scale synthesis of target compounds.

Description

technical field [0001] The invention relates to a synthetic method of an organic compound, in particular to a synthetic method of triptolide. The structure of triptolide is shown in compound 1 in Formula 1. [0002] technical background [0003] Triptolide, also known as triptolide, is an active ingredient isolated from the traditional Chinese medicine Triptolide. Literature discloses that the compound has good antitumor activity, and the compound has also been found to have good activity in immunosuppression, male contraceptives, and the like. [0004] The synthesis of triptolide has been reported since 1977, and so far the following synthetic methods have been reported. [0005] Literature (G.A.Berchtold et al, J.Am.Chem.Soc., 1980,102,1200; J.Org.Chem., 1982,47,2364) discloses that 6-methoxy-1-tetralone is A method for synthesizing triptolide from starting materials (see formula 2). This method completes isopropylation through eight-step reaction, and obtains 6-iso...

Claims

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Application Information

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IPC IPC(8): C07J73/00C07B53/00B01J31/02A61P35/00A61P37/06A61P15/16
CPCY02P20/55
Inventor 高强薛吉军郑保富刘荣
Owner SHANGHAI HAOYUAN CHEMEXPRESS
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