Total synthesis of 1-oxomiltirone via Suzuki coupling

doi:10.1007/s13659-013-0034-7

Natural Products and Bioprospecting ›› 2013, Vol. 3 ›› Issue (3): 117-120.DOI: 10.1007/s13659-013-0034-7

• Short Communication • Previous Articles

Total synthesis of 1-oxomiltirone via Suzuki coupling

Chun-Miao LI^a,c, Hui-Chun GENG^a,b, Ming-Ming LI^a, Gang XU^a, Tie-Jun LING^c, Hong-Bo QIN^a

a State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, China;
b University of Chinese Academy of Sciences, Beijing 100049, China;
c Key Laboratory of Tea Biochemistry and Biotechnology of Ministry of Education & Ministry of Agriculture, Anhui Agricultural University, Hefei 230036, China

Received:2013-04-22 Revised:2013-05-20 Online:2018-02-11 Published:2013-06-24

Total synthesis of 1-oxomiltirone via Suzuki coupling

Chun-Miao LI^a,c, Hui-Chun GENG^a,b, Ming-Ming LI^a, Gang XU^a, Tie-Jun LING^c, Hong-Bo QIN^a

a State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, China;
b University of Chinese Academy of Sciences, Beijing 100049, China;
c Key Laboratory of Tea Biochemistry and Biotechnology of Ministry of Education & Ministry of Agriculture, Anhui Agricultural University, Hefei 230036, China

通讯作者: Hong-Bo QIN,E-mail:qinhongbo@mail.kib.ac.cn;Tie-Jun LING,E-mail:lingtj@ahau.edu.cn

Abstract

Abstract: Abietane diterpenes and miltirone series have shown important activities and for medical purposes in order to achieve the total synthesis of 1-oxomiltrone 1 and miltirone 4, a versatile intermediate 6 was found. The compound 6 could be used as a precursor A-B-C rings with different oxidative degrees in selected abietane diterpenes when synthesized through high yield Suzuki reaction and subsequent cyclization, and total synthesis of 1-oxomiltirone (1) has been achieved.

Key words: total synthesis, Suzuki coupling, 1-oxomiltirone, abietane diterpenes, versatile intermediate

摘要： Abietane diterpenes and miltirone series have shown important activities and for medical purposes in order to achieve the total synthesis of 1-oxomiltrone 1 and miltirone 4, a versatile intermediate 6 was found. The compound 6 could be used as a precursor A-B-C rings with different oxidative degrees in selected abietane diterpenes when synthesized through high yield Suzuki reaction and subsequent cyclization, and total synthesis of 1-oxomiltirone (1) has been achieved.

关键词: total synthesis, Suzuki coupling, 1-oxomiltirone, abietane diterpenes, versatile intermediate

Chun-Miao LI, Hui-Chun GENG, Ming-Ming LI, Gang XU, Tie-Jun LING, Hong-Bo QIN. Total synthesis of 1-oxomiltirone via Suzuki coupling[J]. Natural Products and Bioprospecting, 2013, 3(3): 117-120.

Chun-Miao LI, Hui-Chun GENG, Ming-Ming LI, Gang XU, Tie-Jun LING, Hong-Bo QIN. Total synthesis of 1-oxomiltirone via Suzuki coupling[J]. 应用天然产物, 2013, 3(3): 117-120.

[1]	Song-Yu Hou, Bing-Chao Yan, Han-Dong Sun, Pema-Tenzin Puno. Recent advances in the application of [2+2] cycloaddition in the chemical synthesis of cyclobutane-containing natural products [J]. Natural Products and Bioprospecting, 2024, 14(5): 37-37.
[2]	Aluru Rammohan, Albert F. Khasanov, Dmitry S. Kopchuk, Duvvuru Gunasekar, Grigory V. Zyryanov, Oleg N. Chupakhin. Assessment on facile Diels–Alder approach of α-pyrone and terpenoquinone for the expedient synthesis of various natural scaffolds [J]. Natural Products and Bioprospecting, 2022, 12(2): 12-12.
[3]	Ding Lin, Senze Jiang, Ailian Zhang, Tong Wu, Yongchang Qian, Qingsong Shao. Structural derivatization strategies of natural phenols by semi-synthesis and total-synthesis [J]. Natural Products and Bioprospecting, 2022, 12(2): 8-8.
[4]	Yi Chen, Song-Wei Li, Fang-Zhou Yin, Min Yang, Xia-Juan Huan, Ze-Hong Miao, Xiao-Ming Wang, Yue-Wei Guo. Lagerindicine, a New Pyrrole Alkaloid Isolated from the Flowers of Lagerstroemia indica Linnaeus [J]. Natural Products and Bioprospecting, 2021, 11(1): 73-79.
[5]	Wen-Dan Xu, Liang-Qun Li, Ming-Ming Li, Hui-Chun Geng, Hong-Bo Qin. Catalytic Asymmetric Formal Total Synthesis of (2)-Triptophenolide and (+)-Triptolide [J]. Natural Products and Bioprospecting, 2016, 6(3): 183-186.
[6]	Xianfu Shen, Yongyun Zhou, Yongkai Xi, Jingfeng Zhao, Hongbin Zhang. Total Synthesis of Dimeric HPI Alkaloids [J]. Natural Products and Bioprospecting, 2016, 6(2): 117-139.
[7]	Qi-Long Zhou, Hui-Jing Wang, Pei Tang, Hao Song, Yong Qin. Total Synthesis of Lignan Lactone(-)-Hinokinin [J]. Natural Products and Bioprospecting, 2015, 5(5): 255-261.
[8]	Yang YANG. Total synthesis and determination of the absolute configuration of a natural analgesic: crotonine [J]. Natural Products and Bioprospecting, 2013, 3(6): 288-294.
[9]	Tao XU, Shi-Zhi JIANG, Huai-Rong LUO, Yu-Rong YANG. One-step synthesis of Lycopodium alkaloid(-)-huperzine W via Suzuki-Miyaura coupling [J]. Natural Products and Bioprospecting, 2012, 2(6): 255-257.

Total synthesis of 1-oxomiltirone via Suzuki coupling

Total synthesis of 1-oxomiltirone via Suzuki coupling

PDF (PC)

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 9

Recommended Articles

Metrics

Comments