4-Hydroxy-2-pyrones: Synthesis, Natural Products, and Application

被引:0
|
作者
Fedin, Vladislav V. [1 ]
Obydennov, Dmitrii L. [1 ]
Usachev, Sergei A. [1 ]
Sosnovskikh, Vyacheslav Y. [1 ]
机构
[1] Ural Fed Univ, Inst Nat Sci & Math, Ekaterinburg 620000, Russia
来源
ORGANICS | 2023年 / 4卷 / 04期
基金
俄罗斯科学基金会;
关键词
2-pyrone; 4-pyrone; 4-hydroxy-2-pyrone; triacetic acid lactone; polyketide; cyclization; ketene; ketoacetylene; biological activity; natural products; BIOMIMETIC TOTAL SYNTHESES; ALPHA-PYRONE DERIVATIVES; TRIACETIC ACID LACTONE; 1ST TOTAL-SYNTHESIS; ONE-POT SYNTHESIS; BIOLOGICAL EVALUATION; CYERCENE-A; BIOSYNTHESIS; SALINIPYRONE; SESQUICILLIN;
D O I
10.3390/org4040037
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
4-Hydroxy-2-pyrones are of interest as potential biorenewable molecules for a sustainable transition from biomass feedstock to valuable chemical products. This review focuses on the methodologies for the synthesis of 4-hydroxy-2-pyrones published over the last 20 years. These pyrones as polyketides are widespread in Nature and possess versatile bioactivity that makes them an attractive target for synthesis and modification. Biosynthetic paths of the pyrones are actively developed and used as biotechnological approaches for the construction of natural and unnatural polysubstituted 4-hydroxy-2-pyrones. The major synthetical methods are biomimetic and are based on the cyclization of tricarbonyl compounds. Novel chemical methods of de novo synthesis based on alkyne cyclizations using transition metal complexes and ketene transformations allow for straightforward access to 4-hydroxy-2-pyrones and have been applied for the construction of natural products. Possible directions for further pyrone ring modification are discussed.
引用
收藏
页码:539 / 561
页数:23
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