Synthesis of A-B-C-ring Tricyclic Core of iso-Merrilactone A

doi:10.1007/s40242-019-9064-y

高等学校化学研究 ›› 2019, Vol. 35 ›› Issue (5): 817-822.doi: 10.1007/s40242-019-9064-y

Synthesis of A-B-C-ring Tricyclic Core of iso-Merrilactone A

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:2019-03-05 出版日期:2019-10-01 发布日期:2019-09-24
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).

Synthesis of A-B-C-ring Tricyclic Core of iso-Merrilactone A

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:2019-03-05 Online:2019-10-01 Published:2019-09-24
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： A desymmetrization approach for the synthesis of the A-B-C tricycle intermediate of iso-merrilactone A was described. The key steps of this synthesis to efficiently access the tetracyclic Illicium sesquiterpenes core included an intramolecular aldol cyclization and an oxidative lactonization reaction. A novel Au catalyzed hydrolytic cyclorearrangement cascade reaction was explored in the initial stage.

关键词: Sesquiterpene, Regio-isomer, Cyclorearrangement, Lactonization

Abstract: A desymmetrization approach for the synthesis of the A-B-C tricycle intermediate of iso-merrilactone A was described. The key steps of this synthesis to efficiently access the tetracyclic Illicium sesquiterpenes core included an intramolecular aldol cyclization and an oxidative lactonization reaction. A novel Au catalyzed hydrolytic cyclorearrangement cascade reaction was explored in the initial stage.

Key words: Sesquiterpene, Regio-isomer, Cyclorearrangement, Lactonization

TONG Jie, LIU Chang, WANG Bo. Synthesis of A-B-C-ring Tricyclic Core of iso-Merrilactone A[J]. 高等学校化学研究, 2019, 35(5): 817-822.

TONG Jie, LIU Chang, WANG Bo. Synthesis of A-B-C-ring Tricyclic Core of iso-Merrilactone A[J]. Chemical Research in Chinese Universities, 2019, 35(5): 817-822.

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Synthesis of A-B-C-ring Tricyclic Core of iso-Merrilactone A

Synthesis of A-B-C-ring Tricyclic Core of iso-Merrilactone A

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