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Method for asymmetrically synthesizing Triptonide and Triptolide

An asymmetric and unsaturated technology, applied in asymmetric synthesis, chemical instruments and methods, organic chemistry methods, etc., can solve the problems of low synthesis efficiency and long steps

Active Publication Date: 2021-08-24
PEKING UNIV
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  • Abstract
  • Description
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  • Application Information

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Problems solved by technology

However, these routes have long steps and low synthesis efficiency

Method used

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  • Method for asymmetrically synthesizing Triptonide and Triptolide
  • Method for asymmetrically synthesizing Triptonide and Triptolide
  • Method for asymmetrically synthesizing Triptonide and Triptolide

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Embodiment Construction

[0061] The present invention will be described in further detail below by way of examples.

[0062] Synthesis of compound 2:

[0063]

[0064] To the CH of compound 1 (2g, 17.9mmol) 2 Cl 2 (88 mL) was added S1 (5.4 mL, 35.7 mmol) followed by Hoveyda-Grubbs second generation catalyst (276 mg, 0.45 mmol). Connect the flask to a condenser, replace the nitrogen, and then place the reaction system in an oil bath at 45°C. After 4 hours, add Hoveyda-Grubbs second-generation catalyst (276mg, 0.45mmol) and S1 (5.4mL, 35.7mmol) to continue After reacting at 45°C for 12 hours, the reaction system was cooled to room temperature. The solvent was spun off in vacuo, and the residue was purified by column chromatography (silica gel, petroleum ether / ethyl acetate=10:1 to 5:1) to obtain compound 2, a colorless oil, 2.6 g, 12.1 mmol, yield 68%.

[0065] The detection data of compound 2 are as follows:

[0066] R f =0.31 (petroleum ether / ethyl acetate=2:1)

[0067]

[0068] HRMS-ESI(...

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Abstract

The invention discloses a method for asymmetrically synthesizing triptonide and triptolide, the method comprises the following steps: starting from (-)-Taniguchi lactone, developing a framework structure of the triptolide through alkylation reaction, transition metal catalytic hydrogen atom transfer reaction and aldol type ring closing reaction, further completing total synthesis of the triptonide through oxidation reaction, and converting the triptonide into the triptolide through a known reduction reaction. The reaction operation in the synthesis is simple, the method can be widely popularized and used, and a foundation is laid for further structure-function relationship research and structure optimization of the triptolide and the triptolide.

Description

technical field [0001] The invention belongs to the field of organic chemical synthesis, and relates to a method for asymmetrically synthesizing triptonide and triptolide based on a metal-catalyzed hydrogen atom transfer reaction. Background technique [0002] Tripterygium wilfordii has a long history of medicinal use in China, and has been used in the treatment of rheumatoid arthritis, systemic lupus erythematosus and various skin diseases. Triptolide (triptolide, also known as triptolide) is the main active ingredient of triptolide, which has anti-inflammatory, anti-cancer, immunosuppressive and other physiological activities; And triptolide itself has a variety of important biological activities, including as a potential non-hormonal male contraceptive. These two compounds have low content in nature, poor water solubility, and large toxic and side effects, which limit their clinical application. They have extremely important research value for the synthesis and structura...

Claims

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Application Information

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IPC IPC(8): C07J73/00C07B53/00
CPCC07J73/003C07B53/00C07B2200/07
Inventor 罗佗平房显赫张楠陈思聪
Owner PEKING UNIV
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