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Chiral gamma, gamma-disubstituted butenolide compound and preparation method thereof

A butenolide and compound technology, applied in the field of chiral γ, can solve the problems of large steric hindrance of substituents and limitation of product structure diversity, etc.

Active Publication Date: 2020-06-19
INST OF PHARMACY SHANDONG PROV ACAD OF MEDICAL SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although great progress has been made, the substituents of the donor are relatively hindered. structural diversity

Method used

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  • Chiral gamma, gamma-disubstituted butenolide compound and preparation method thereof
  • Chiral gamma, gamma-disubstituted butenolide compound and preparation method thereof
  • Chiral gamma, gamma-disubstituted butenolide compound and preparation method thereof

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Experimental program
Comparison scheme
Effect test

Embodiment Construction

[0025] Chiral thiourea bifunctional catalysts I-VII of the present invention:

[0026]

[0027] 1. Compound 3aa: Take compound 1a (0.25mmol) and chiral thiourea bifunctional catalyst VII (0.05mmol), add solvent dioxane (2mL), add compound 2a (0.50mmol), and stir to react. After the reaction was completed, it was quenched with saturated ammonium chloride solution, extracted with ethyl acetate, filtered with suction, and spin-dried. The eluent was ethyl acetate:petroleum ether=1:5 for separation and purification, and spin-dried to obtain compound 3aa.

[0028]

[0029] Yield: 95%. Silica gel column chromatography (ethyl acetate / petroleum ether=1:5); 1 H NMR (400MHz, CDCl 3 ) δ7.88(1H,s), δ7.39–7.28(3H,m), δ7.20–7.15(2H,m), δ4.85(1H,dd, J=13.4,5.0Hz), δ4. 76 (1H, dd, J = 13.3, 10.0Hz), δ4.27 (2H, q, J = 7.1Hz), δ 4.11 (1H, dd, J = 9.9, 5.0Hz), δ2.02 (1H, dq ,J=14.8,7.4Hz),δ1.85(1H,dq, J=14.7,7.4Hz),δ1.31(3H,t,J=7.1Hz),δ0.88(3H,t,J=7.4 Hz). 13 C NMR (100MHz, CDCl 3 )δ...

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Abstract

The invention discloses a chiral gamma, gamma-disubstituted butenolide compound and a preparation method thereof. Chiral gamma, gamma-disubstituted butenolide compounds widely exist in various naturalproducts, have important biological activity, and are also important intermediates for constructing polyterpene compounds and medicines. According to the application, a series of chiral gamma, gamma-disubstituted butenolide compounds with the yield as high as 98% and the stereoselectivity greater than 20: 1dr and 99% ee are synthesized through a vinylogous Michael addition reaction of gamma-dimerfuranone catalyzed by a bifunctional thiourea catalyst and alpha, beta-unsaturated nitroolefin. According to the method, the functional gamma, gamma-disubstituted butenolide compound with multiple chiral centers can be conveniently, quickly and efficiently obtained.

Description

technical field [0001] The invention belongs to the field of pharmaceutical compound synthesis, and relates to a chiral γ, γ-disubstituted butenolide compound and a preparation method thereof. Background technique [0002] Chiral γ, γ-disubstituted butenolides are the core structural units of many natural products and pharmaceutically active compounds. Most of the methods are achieved by asymmetrically catalyzed Michael addition of γ-substituted divinyl alcohols or 5-substituted 2-(trimethylsiloxy)furans with different Michael receptor. Over the past decade, various groups have developed various methods to synthesize these important components. Although great progress has been made, the substituents of the donor are relatively hindered, for example, there are basically no substituents at the 3-position and 4-position, and the 5-position is mainly methyl, benzyl and aryl, which limits the structural diversity of the products. [0003] Therefore, there is an urgent need fo...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/68
CPCC07D307/68C07B2200/07
Inventor 白著双张才荣陈泳怡刘爱芹王新宇刘学超严楚娜庞靖祥朱文宁诸葛慧
Owner INST OF PHARMACY SHANDONG PROV ACAD OF MEDICAL SCI
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