Natural product (+)-Strictifolione synthetic method

A technology of natural products and synthetic methods, applied in chemical recovery, organic chemistry and other directions, can solve the problems of high synthesis cost and long route, and achieve the effects of simple operation, good reaction selectivity and lower production cost.

Inactive Publication Date: 2016-01-20
JIANGXI SCI & TECH NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] The purpose of the present invention is to overcome the problems such as long route and expensive synthesis cost in existing synthetic methods, and provides a new synthetic method of natural product (+)-Strictifolione

Method used

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  • Natural product (+)-Strictifolione synthetic method
  • Natural product (+)-Strictifolione synthetic method
  • Natural product (+)-Strictifolione synthetic method

Examples

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Embodiment 1

[0029] 1) Under the protection of nitrogen, dissolve the Evans chiral auxiliary (0.47g, 1.87mmol) of formula 2 in dichloromethane (20mL), cool down to -78°C and slowly add titanium tetrachloride (TiCl 4 ) (0.21mL, 1.91mmol); 5 minutes later, N, N-diisopropylethylamine (DIPEA) (0.364mL, 2.09mmol) was added and reacted for 30 minutes; then 3-phenylpropanal (0.285mL, 2.06 mmol) was dissolved in 10 mL of dichloromethane and added dropwise; after 30 minutes, it was quenched with saturated ammonium chloride, extracted with dichloromethane, spin-dried and passed through the column, and concentrated to obtain a yellow solid, that is, the compound of formula 3, yield: 60 %;

[0030] Dissolve the prepared compound 3 (0.3g, 0.78mmol) in tetrahydrofuran (8mL), cool down to -78°C and slowly add diisobutylaluminum hydride (DIBAL-H) ​​(2.33mL, 1MinHexane) and react for 20 minutes Diluted with a small amount of ethyl acetate, quenched by adding 4 mL of saturated potassium sodium tartrate, an...

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Abstract

The invention discloses a natural product (+)-Strictifolione synthetic method. The method comprises the steps that 3-benzenepropanal and an Evans chiral auxiliary reagent are subjected to an aldol reaction for diisobutyl aluminum hydride reduction and then subjected to an addition reaction with metal indium activated 3-propylene bromine to obtain a compound shown in the formula 5; silyl enol ether reacts with acrolein under the action of titanium tetraisopropoxide and (R)-1,1-binaphthol, then carbonyl is reduced through sodium borohydride, p-toluenesulfonic acidpyridinium salt is used for cyclization, and acidification treatment is carried out after a methylsulfonyl group becomes a leaving group to obtain a compound shown in the formula 11; a Grubbs second-generation catalyst is used for carrying out a metal coupling reaction on the compounds shown in the formulas 5 and 11 to obtain (+)-Strictifolione. According to the bisection synthetic method, the design is simple and reasonable, operation is easy and convenient, the reaction condition is moderate, linear steps are simple, the product yield is high, and the production cost is greatly reduced.

Description

technical field [0001] The invention relates to a synthesis method of a key intermediate of an antifungal drug, in particular to a synthesis method of a natural product (+)-Strictifolione. Background technique [0002] In recent years, with the increasing application of immunosuppressants, corticosteroids, and broad-spectrum antibiotics, the rate of fungal infections, especially deep fungal infections, has risen sharply. Although antifungal infections have made great progress from prevention to treatment, the treatment of deep fungal infections still faces many challenges, such as: the types of fungal infections are constantly changing, fungi are mutating rapidly, and drug-resistant strains continue to emerge; in addition , the existing antifungal drugs have serious side effects and are prone to drug resistance, so the demand for antifungal drugs is increasing day by day. [0003] The natural product (+)-Strictifolione was isolated from the bark of Cryptocarya strictifolia ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D309/30
CPCY02P20/582C07D309/30
Inventor 王晓季王高鹏黄双平张志滨刘帅陈世鹏
Owner JIANGXI SCI & TECH NORMAL UNIV
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