Icaritin synthesis

5synthesis methods

Product Name:Icaritin
CAS Number:118525-40-9
Molecular formula:C21H20O6
Molecular Weight:368.38

Icaritin, the aglycone of icariin, has many pharmacological and biological activities, such as antiosteoporosis activity and estrogen regulation.The novel total synthesis of icaritin, naturally occurring with important bioactive 8-prenylflavonoid, was performed via a reaction sequence of 8 steps including Baker-Venkataraman reaction, chemoselective benzyl or methoxymethyl protection, dimethyldioxirane (DMDO) oxidation, O-prenylation, Claisen rearrangement and deprotection, starting from 2,4,6-trihydroxyacetophenone and 4-hydroxybenzoic acid in overall yields of 23%. The key step was Claisen rearrangement under microwave irradiation.
Total Synthesis of Icaritin via Microwave-assistance Claisen Rearrangement

113558-15-9 Synthesis

113558-15-9
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118525-40-9
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Yield:118525-40-9 82%

Reaction Conditions:

with sulfuric acid in ethanol;water at 50; for 5 h;

Steps:

1.2 3,5,7-trihydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-4H-chromen-4-one
Concentrated sulfuric acid (20 mL) was slowly added dropwise to a mixed solvent of ethanol and water (V / V = 1/1, 200 mL), followed by addition of 5,7-dihydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-3-(((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-4H-chromen-4-one (6 g, 11.7 mmol) and the reaction mixture was stirred at 50 ° C for 5 hours and concentrated under reduced pressure. The residue was added to 100 mL of water and stirred for 30 minutes. The mixture was extracted with ethyl acetate (50 mL x 3) and the combined organic layers were washed with saturated sodium chloride solution (30 mL) and dried over anhydrous sodium sulfate. The organic phase was concentrated under reduced pressure and the residue was recrystallized from ethyl acetate to give the title compound as a yellow solid (3.5 g, 82%).

References:

Guangdong East Sunshine Pharmaceutical Co., Ltd.;Zhang, Yingjun;Zhou, Pingjian;Wang, Xiaojun;Yang, Chuanwen CN104530127, 2016, B Location in patent:Paragraph 0156-0157; 0161-0162

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