Improved Synthesis of Icaritin and Total Synthesis of β -Anhydroicaritin

doi:10.1007/s40242-019-9012-x

高等学校化学研究 ›› 2019, Vol. 35 ›› Issue (4): 616-620.doi: 10.1007/s40242-019-9012-x

Improved Synthesis of Icaritin and Total Synthesis of β -Anhydroicaritin

TONG Jie^1,2, LIU Chang¹, WANG Bo^1,3

1. CAS Key Laboratory of High-performance Synthetic Rubber and Its Composite Materials, Key Laboratory of Green Chemistry and Process of Jilin Province, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Changchun 130022, P. R. China;
2. University of Chinese Academy of Sciences, Beijing 100049, P. R. China;
3. University of Science and Technology of China, Hefei 230026, P. R. China

收稿日期:2019-01-14 修回日期:2019-04-03 出版日期:2019-08-01 发布日期:2019-08-01
通讯作者: LIU Chang, WANG Bo E-mail:wangbo@ciac.ac.cn;liuchang1010@ciac.ac.cn
基金资助:
Supported by the National Natural Science Foundation of China(No.21672203).

Improved Synthesis of Icaritin and Total Synthesis of β -Anhydroicaritin

TONG Jie^1,2, LIU Chang¹, WANG Bo^1,3

1. CAS Key Laboratory of High-performance Synthetic Rubber and Its Composite Materials, Key Laboratory of Green Chemistry and Process of Jilin Province, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Changchun 130022, P. R. China;
2. University of Chinese Academy of Sciences, Beijing 100049, P. R. China;
3. University of Science and Technology of China, Hefei 230026, P. R. China

Received:2019-01-14 Revised:2019-04-03 Online:2019-08-01 Published:2019-08-01
Contact: LIU Chang, WANG Bo E-mail:wangbo@ciac.ac.cn;liuchang1010@ciac.ac.cn
Supported by:
Supported by the National Natural Science Foundation of China(No.21672203).

摘要/Abstract

摘要： Natural products icaritin and β-anhydroicaritin with P-glycoprotein(P-gp) inhibitory activities were efficiently synthesized in nine steps from commercially available phloroglucinol. A modified Algar-Flynn-Oyamada cyclization and relay Claisen-Cope rearrangement were employed in this concise route. Our synthesis offers opportunities to synthesize various icariin analogues for biological and pharmacological investigations.

关键词: Icaritin, Flavonol, Regioselectivity, Algar-Flynn-Oyamada

Abstract: Natural products icaritin and β-anhydroicaritin with P-glycoprotein(P-gp) inhibitory activities were efficiently synthesized in nine steps from commercially available phloroglucinol. A modified Algar-Flynn-Oyamada cyclization and relay Claisen-Cope rearrangement were employed in this concise route. Our synthesis offers opportunities to synthesize various icariin analogues for biological and pharmacological investigations.

Key words: Icaritin, Flavonol, Regioselectivity, Algar-Flynn-Oyamada

TONG Jie, LIU Chang, WANG Bo. Improved Synthesis of Icaritin and Total Synthesis of β -Anhydroicaritin[J]. 高等学校化学研究, 2019, 35(4): 616-620.

TONG Jie, LIU Chang, WANG Bo. Improved Synthesis of Icaritin and Total Synthesis of β -Anhydroicaritin[J]. Chemical Research in Chinese Universities, 2019, 35(4): 616-620.

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Improved Synthesis of Icaritin and Total Synthesis of β -Anhydroicaritin

Improved Synthesis of Icaritin and Total Synthesis of β -Anhydroicaritin

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