SIOC English
有机化学
高级检索

有机化学 >

2021 , Vol. 41 >Issue 7: 2636 - 2649

DOI: https://doi.org/10.6023/cjoc202101041

综述与进展

倍半萜生物碱Dendrobine的全合成研究进展

  • 肖检 ,
  • 彭羽 ,
  • 李卫东
展开
  • a 西南交通大学生命科学与工程学院 四川省天然药物仿生合成工程研究中心 成都 610031
    b 伊犁师范大学 新疆天然产物化学与应用重点实验室 新疆伊宁 835000

收稿日期: 2021-01-25

  修回日期: 2021-02-21

  网络出版日期: 2021-03-12

基金资助

国家自然科学基金(21772078); 中央高校基本科研业务费专项资金(2682019CX70); 中央高校基本科研业务费专项资金(2682019CX71); 中央高校基本科研业务费专项资金(2682020CX55); 新疆维吾尔自治区高校科研计划项目(重点项目)(XJEDU2018I018)

收起

Advances on the Total Synthesis of Sesquiterpenoid Alkaloid Dendrobine

  • Jian Xiao ,
  • Yu Peng ,
  • Wei-Dong Z. Li
Expand
  • a Engineering Research Center Biomimetic Synthesis of Natural Drugs of Sichuan Province, School of Life Science and Engineering, Southwest Jiaotong University, Chengdu 610031
    b Key Lab of Natural Product Chemistry and Application in Xinjiang, Yili Normal University, Yining, Xinjiang 835000
* Corresponding author. E-mail:

Received date: 2021-01-25

  Revised date: 2021-02-21

  Online published: 2021-03-12

Supported by

National Natural Science Foundation of China(21772078); Fundamental Research Funds for the Central Universities(2682019CX70); Fundamental Research Funds for the Central Universities(2682019CX71); Fundamental Research Funds for the Central Universities(2682020CX55); Program of Natural Science Foundation of Xinjiang Autonomous Region Colleges (Key Program)(XJEDU2018I018)

Fold

摘要

石斛碱(Dendrobine)是一类从传统中药金钗石斛中分离得到的具有Picrotoxane倍半萜碳骨架的生物碱类天然产物. 由于该化合物具有多环稠合和七个连续立体中心的结构特点, 以及镇痛和退热等药理活性, 引起了众多有机合成化学家和药物化学家的关注. 五十年来, 天然产物Dendrobine的药理活性研究和化学合成不断涌现, 主要总结了天然产物Dendrobine的生源途径和合成研究进展.

关键词： 天然产物; 倍半萜生物碱; 石斛碱; 全合成; 木防己毒烷

本文引用格式

肖检 , 彭羽 , 李卫东 . 倍半萜生物碱Dendrobine的全合成研究进展[J]. 有机化学, 2021 , 41(7) : 2636 -2649 . DOI: 10.6023/cjoc202101041

Abstract

Dendrobine is an important sesquiterpenoid alkaloid bearing the picrotoxane carbon skeleton isolated from the traditional Chinese medicine “Chin-Shih-Hu”. Because of structural characteristics of fused polycyclic and seven contiguous stereocenters, and exhibiting analgesic, antipyretic activities, dendrobine has attracted a great deal of attentions from both synthetic organic chemists and medicinal chemists. Over the past 50 years, there has been a number of research reports on the pharmacological activities and chemical synthesis of dendrobine. This review summarizes the biosynthetic hypothesis and synthetic advances on dendrobine.

Key words： natural product; sesquiterpenoid alkaloid; dendrobine; total synthesis; picrotoxane

参考文献

[1]
Pharmacopoeia Committee of Ministry of Health, Chinese Pharmacopoeia, 2005 Edition I, Chemical Industry Press, Beijing, 2005, p.62 (in Chinese).
[1]
(中华人民共和国卫生部药典委员会, 中华人民共和国药典2005年版一部, 化学工业出版社, 北京, 2005, p. 62.)
[2]
(a) Suzuki, H.; Keimatsu, I.; Ito, K. Yakugaku Zasshi 1932, 52,1049.
[2]
(b) Suzuki, H.; Keimatsu, I.; Ito, K. J. Pharm. Soc. Jpn. 1934, 54,802.
[3]
(a) Chen,K. K.; Chen,A. L. J. Biol. Chem. 1935, 111,653.
[3]
(b) Chen,K. K.; Chen,A. L. J. Pharmacol. 1935, 55,319.
[4]
(a) Inubushi, Y.; Sasaki, Y.; Tsuda, Y.; Yasui, B.; Konita, T.; Matsumoto, J.; Katarao, E. Nakano, J. Yakugaku Zasshi 1963, 83,1184.
[4]
(b) Yamamura, S.; Hirata, Y. Tetrahedron Lett. 1964, 5,79.
[4]
(c) Onaka, T.; Kamata, S.; Maeda, T.; Kawazoe, Y.; Natsume, M.; Okamoto, T.; Uchimaru, F.; Shimizu, M. Chem. Pharm. Bull. 1964, 12,506.
[4]
(d) Huang,W. -K. Acta Chim. Sinica 1965, 31,333 (in Chinese).
[4]
( 黄文魁, 化学学报, 1965, 31,333.)
[4]
(e) Guo, L.; Frey, W.; Plietker, B. Org. Lett. 2018, 20,4328.
[5]
(a) Okamoto, T.; Natsume, M.; Onaka, T.; Uchimaru, F.; Shimizu, M. Chem. Pharm. Bull. 1966, 14,672.
[5]
(b) Morita, H.; Fujiwara, M.; Yoshida, N.; Kobayashi, J. Tetrahedron 2000, 56,5801.
[5]
(c) Meng,C. -W.; He,Y. -L.; Peng, C.; Ding,X. -J.; Xiong, L. Fitoterapia 2017, 121,206.
[6]
(a) Li, R.; Liu, T.; Liu, M.; Chen, F.; Liu, S.; Yang, J. J. Agric. Food Chem. 2017, 65,3665.
[6]
(b) X,Y. -Y.; Xu,Y. -S.; Wang, Y.; Wu, Q.; Lu,Y. -F.; Liu, J.; Shi,J. -S.. J. Pharm. Pharmacol. 2017, 69,1409.
[6]
(c) Song,T. -H.; Chen,X. -X.; Lee,C. K.-F.; Sze,S. C.-W.; Feng,Y. -B.; Yang,Z. -J.; Chen,H. -Y.; Li,S. -T.; Zhang,L. -Y.; Wei, G.; Shi, J.; Xu, K.; Ng,T. -B.; Zhu,L. -L.; Zhang,K. -Y. Phytomedicine 2019, 53,18.
[7]
(a) Cross,A. D. Rev. Chem. Soc. 1960, 14,317.
[7]
(b) Kolbe, M.; Westfelt, L. Acta Chem. Scand. 1967, 21,585.
[7]
(c) Kolbe-Haugwitz, M.; Westfelt, L. Acta Chem. Scand. 1970, 24,1623.
[7]
(d) Yamazaki, M.; Matsuo, M.; Arai, K. Chem. Pharm. Bull. 1966, 14,1058.
[7]
(e) Biollaz, M.; Arigoni, D. J. Chem. Soc.,Chem. Commun. 1969,633.
[7]
(f) Arigoni, D. Pure Appl. Chem. 1975, 41,219.
[7]
(g) Hanson,J. R.; Nyfeler, R. J. Chem. Soc.,Chem. Commun. 1975,171.
[7]
(h) Hanson,J. R.; Nyfeler, R. J. Chem. Soc.,Chem. Commun. 1975,824.
[7]
(i) Corbella, A.; Gariboldi, P.; Jommi, G. J. Chem. Soc.,Chem. Commun. 1973,729.
[7]
(j) Corbella, A.; Gariboldi, P.; Jommi, G. Sisti, M. J. Chem. Soc.,Chem. Commun. 1975,288.
[7]
(k) Cordell,A. G. Chem. Rev. 1976, 76,425.
[7]
(l) Li, Q.; Ding, G.; Li, B.; Guo,S. -X. Sci. Rep. 2017, 7,316.
[8]
(a) Yamamoto, K.; Kawasaki, I.; Kaneko, T. Tetrahedron Lett. 1970,4859.
[8]
(b) Kende,A. S.; Bentley,T. J.; Mader,R. A.; Ridge, D. J. Am. Chem. Soc. 1974, 96,4332.
[8]
(c) Hu,Q. -Y.; Zhou, G.; Corey,E. J. J. Am. Chem. Soc. 2004, 126,13708.
[9]
Yamada, K.; Suzuki, M.; Hayakawa, Y.; Aoki, K.; Nakamura, H.; Nagase, H.; Hirata, Y. J. Am. Chem. Soc. 1972, 94,8278.
[10]
(a) Mori, M.; Uesaka, N.; Shibasaki, M. J. Org. Chem. 1992, 57,3519.
[10]
(b) Mori, M.; Uesaka, N.; Shibasaki, M.; Saitoh, F. Chem. Lett. 1993,213.
[10]
(c) Mori, M.; Uesaka, N.; Shibasaki, M.; Saitoh, F.; Okamura, K.; Date, T. J. Org. Chem. 1994, 59,5633.
[10]
(d) Takano, S.; Inomata, K.; Ogasawara, K. Chem. Lett. 1992,443.
[10]
(e) Cassayre, J.; Zard,S. Z. J. Am. Chem. Soc. 1999, 121,6072.
[11]
(a) Lee,C. H.; Westling, M.; Livinghouse, T.; Williams,A. C. J. Am. Chem. Soc. 1992, 114,4089.
[11]
(b) Lee, Y.; Rochette,E. M.; Kim, J.; Chen,D. Y.-K. Angew. Chem.,Int. Ed. 2017, 56,12250.
[11]
(c) Teichert,J. F.; Zhang, S.; Zijl, V.; Slaa,J. W.; Minnaard,A. J.; Feringa,B. L. Org. Lett. 2010, 12,4685.
[12]
Inubushi, Y.; Kikuchi, T.; Ibuka, T.; Tanaka, T.; Saji, I.; Tokane, K. J. Chem. Soc.,Chem. Commun. 1972,1252.
[13]
(a) Martin,S. F.; Li, W. J. Org. Chem. 1989, 54,268.
[13]
(b) Padwa, A.; Dimitroff, M.; Liu, B. Org. Lett. 2000, 2,3233.
[13]
(c) Padwa, A.; Brodney,M. A.; Dimitroff, M.; Liu, B. Wu,T. -H. J. Org. Chem. 2001, 66,3119.
[14]
(a) Borch,R. F.; Evans,A. J.; Wade, J. J. Am. Chem. Soc. 1975, 97,6282.
[14]
(b) Borch,R. F.; Evans,A. J.; Wade, J. J. Am. Chem. Soc. 1977, 99,1612.
[14]
(c) Roush,W. R. J. Am. Chem. Soc. 1978, 100,3599.
[15]
(a) Trost,B. M.; B.M.; Tasker,A. S.; Ruther, G.; Brandes, A. J. Am. Chem. Soc. 1991, 113,670.
[15]
(b) Sha,C. -K.; Chiu,R. -T.; Yang,C. -F.; Yao,N. -T.; Tseng,W. -H.; Liao,F. -L.; Wang,S. -L. J. Am. Chem. Soc. 1997, 119,4130.
[16]
(a) Brattesani,D. N.; Heathcock,C. H. J. Org. Chem. 1975, 40,2165.
[16]
(b) Kreis,L. M.; Carreira,E. M. Angew. Chem.,Int. Ed. 2012, 51,3436.
[16]
(c) Williams,B. M.; Trauner, D. J. Org. Chem. 2018, 83,3061.
Options
文章导航

/

〈 〉