Asymmetric full-synthesis method of Tanikolide

A fully synthetic, asymmetric technology, applied in the production of bulk chemicals, organic chemistry, etc., can solve problems that are difficult to meet the needs of in-depth research on chemical properties and biological activities

Inactive Publication Date: 2013-05-22
ZHENGZHOU UNIV
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Problems solved by technology

Obviously, relying solely on the amount of natural samples is difficult to meet the n

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  • Asymmetric full-synthesis method of Tanikolide
  • Asymmetric full-synthesis method of Tanikolide
  • Asymmetric full-synthesis method of Tanikolide

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Embodiment Construction

[0029] The above-mentioned content of the present invention will be further described in detail below through specific embodiments in the form of examples, but it should not be understood that the scope of the above-mentioned subject of the present invention is limited to the following examples. All technologies realized based on the above contents of the present invention belong to the scope of this invention.

[0030] The following are the embodiments of the present invention, which are divided into ten steps for the convenience of description.

[0031] step 1:

[0032]

[0033] 332 mg (1.43 mmol) primary alcohol 2 Dissolve in 7 mL CH 2 Cl 2 , add 1 mL H 2 O, then add 67 mg (0.43 mmol) TEMPO, 17 mg (0.14 mmol) KBr, 16 mg (0.18 mmol) NaHCO 3 . After stirring at room temperature for 10 min, 1.29 mL (1.7 mmol, 10%) of NaClO was added to the reaction system within 40 min. After the addition, use 100mL CH 2 Cl 2 Dilute the reaction system, successively with 2 × 10 mL...

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Abstract

The invention discloses an asymmetric full-synthesis method of a natural product (+)-Tanikolide, belonging to the field of organic synthesis. The (+)-Tanikolide has a structure as shown in the specification; and chiral tertiary alcohol is created through a synthesis strategy which is completely different from that of the existing document, and the synthesis of (+)-Tanikolide is correspondingly selectively finished. The synthesis path takes the optically active amino alcohol as a raw material and comprises the following steps of: performing an oxidation reaction to obtain amino aldehyde with maintained configuration; creating chiral quaternary carbon through three-step continuous reaction including Witting reaction, [2,3]-Meisenheimer rearrangement and catalytic hydrogenation; and finally performing functional group transformation to obtain a target product. The total yield is 35%. The operation is convenient, the reaction conditions are moderate, the method is suitable for large-scale preparation, and the optical rotation of the synthesis product is consistent with the optical rotation and optical rotation direction of the natural product (+)-Tanikolide.

Description

technical field [0001] The invention relates to an asymmetric total synthesis method of natural product (+)-Tanikolide, which belongs to the field of organic synthesis. Background technique [0002] The development and utilization of marine biological resources has been paid more and more attention by the state. Due to the special habitat, marine organisms can produce active substances that terrestrial organisms do not have, which has been recognized by the scientific community. Many foreign literatures have reported that marine microorganisms, even if they are species similar to land, will produce different active substances from land microorganisms due to the special living environment. Therefore, marine microorganisms are considered to be an important resource for obtaining new antibiotics and other active substances in the future, and become a research hotspot at home and abroad. [0003] In 1999, Gernick's group isolated the natural product (+)-Tanikolide for the first...

Claims

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Application Information

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IPC IPC(8): C07D309/30
CPCY02P20/55
Inventor 杨华孙默然谢阳腊周航牛长岭
Owner ZHENGZHOU UNIV
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