- Efficient total synthesis method and application of natural product schaftoside
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The invention belongs to the technical field of chemistry and medicine, and discloses an efficient total synthesis method and application of a natural product schaftoside. The method comprises the steps of subjecting naringenin, tert-butyldimethylsilyl chloride and acetyl chloride to reaction to obtain an intermediate compound 2, and conducting deoxidation reaction to obtain an intermediate compound 3; carrying out rearrangement reaction on the intermediate compound 3 to obtain an intermediate compound 5, and removing a silicon-based protecting group to obtain an intermediate compound 6; carrying out rearrangement reaction on the intermediate compound 6 to obtain an intermediate compound 8; reacting the intermediate compound 8 with benzyl bromide in potassium carbonate to obtain an intermediate compound 9; oxidizing the intermediate compound 9 by ceric ammonium nitrate and pyridinium dichromate to obtain an intermediate compound 10; removing benzyl from the intermediate compound 10 to obtain an intermediate compound 11; and catalyzing the intermediate compound 11 to obtain an intermediate compound 12, and removing acetyl to obtain a target product compound. The method is mild in reaction condition, convenient to operate, economical in raw materials and capable of being used for industrial preparation.
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- Effective total synthesis of schaftoside
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A short and scalable approach toward the total synthesis of schaftoside, a naturally occurring bioactive C-glycosylflavone, has been developed from readily available (±)-naringenin. The highlights of this work are double Lewis acid promoted O→C rearrangement to form C-glycoside, oxidative dehydrogenation to construct flavone ring, and easy operational process to make the target product in multigram-scale.
- Shang, Chengxiang,Zhao, Chuanfang,Nie, Pengpeng,Liu, Jun,Du, Yuguo
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- New C,O-Glycosylflavones from the Genus Silene
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Chromatographic separation of extracts from the aerial parts of three Silene species (Caryophyllaceae) isolated 26 flavonoids including the four new C,O-glycosylflavones acacetin-6-C-(2″-O-β-D-glucopyranosyl)-β-D-glucopyranoside-7-O-β-D-glucopyranoside (s
- Olennikov,Kashchenko
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p. 1026 - 1034
(2020/11/05)
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