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Synthetic method of natural product (+)-strictifolione

A technology of natural products and synthesis 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 optimized production process.

Inactive Publication Date: 2017-08-25
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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  • Synthetic method of natural product (+)-strictifolione
  • Synthetic method of natural product (+)-strictifolione

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Experimental program
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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] The prepared compound 3 (0.3g, 0.78mmol) was dissolved in tetrahydrofuran (8mL), and after cooling to -78°C, diisobutylaluminum hydride (DIBAL-H) ​​(2.33mL, 1M in Hexane) was slowly added, and the reaction After 20 minutes, it was diluted with a small amount of ethyl acetate and then quenched by adding 4 m...

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Abstract

The invention discloses a method for synthesizing natural product (+)-Strictifolione. The present invention utilizes 3-phenylpropanal and Evans chiral auxiliary agent to carry out aldol condensation reaction, then reduces with diisobutyl aluminum hydride, and then adds 3-propylene bromide activated by metal indium to obtain the compound of formula 5; enol Silicone ether reacts with acrolein under the action of titanium tetraisopropoxide and (R)-1,1-binaphthol, then reduces the carbonyl group with sodium borohydride, and then uses pyridinium p-toluenesulfonate for ring closure, and then forms a After the sulfonyl group becomes a leaving group, the acid is added to obtain the compound of formula 11; the compound of formula 5 and the compound of formula 11 are subjected to metal coupling reaction using Grubbs second-generation catalyst to obtain (+)-Strictifolione. The "dichotomy" synthesis method of the present invention is simple and reasonable in design, easy to operate, mild in reaction conditions, less in linear steps, high in product yield, and greatly reduces production cost.

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