Advances on the Total Synthesis of Sesquiterpenoid Alkaloid Dendrobine

doi:10.6023/cjoc202101041

Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (7): 2636-2649.DOI: 10.6023/cjoc202101041 Previous Articles Next Articles

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倍半萜生物碱Dendrobine的全合成研究进展

肖检^a, 彭羽^a^,^b, 李卫东^a^,^b^,^*()

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 发布日期:2021-03-12
通讯作者: 李卫东
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)

Advances on the Total Synthesis of Sesquiterpenoid Alkaloid Dendrobine

Jian Xiao^a, Yu Peng^a^,^b, Wei-Dong Z. Li^a^,^b()

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

Received:2021-01-25 Revised:2021-02-21 Published:2021-03-12
Contact: Wei-Dong Z. Li
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)

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

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Jian Xiao, Yu Peng, Wei-Dong Z. Li. Advances on the Total Synthesis of Sesquiterpenoid Alkaloid Dendrobine[J]. Chinese Journal of Organic Chemistry, 2021, 41(7): 2636-2649.

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Fig. & Tab. 29

Figure 1. Structures of related dendrobine sesquiterpenoid alkaloids

Scheme 1. Biosynthetic hypothesis of picrotoxane skeleton by Cross

Scheme 2. Biosynthetic hypothesis of picrotoxane skeleton by Arigoni

Scheme 3. Biosynthetic hypothesis of Dendrobine

Figure 2. Overview of total synthesis of dendrobine

Figure 3. Strategic key intermediates in the total synthesis of Dendrobine

Scheme 4. Synthetic attempt of dendrobine by Yamamoto's group (1970)

Scheme 5. Total synthesis of (±)-dendrobine by Kende's group (1974)

Scheme 6. Formal synthesis of (–)-dendrobine by Corey's group (2004)

Scheme 7. Formal synthesis of (–)-dendrobine by Mori's group (1992)

Scheme 8. Synthetic study of dendrobine by Takano's group (1992)

Scheme 9. Total synthesis of (–)-dendrobine by Zard's group (1999)

Scheme 10. Total synthesis of (±)-dendrobine by Livinghouse's group (1992)

Scheme 11. Formal synthesis of (±)-dendrobine by Chen's group (2017)

Scheme 12. Total synthesis of (±)-dendrobine by Yamada's group (1972)

Scheme 13. Total synthesis of (±)-dendrobine by Inubushi's group (1972)

Scheme 14. Formal synthesis of (±)-dendrobine by Martin's group (1989)

Scheme 15. Formal synthesis of (±)-dendrobine by Padwa's group (2000)

Scheme 16. Synthesis of 8-epi-dendrobine by Borch's group (1975)

Scheme 17. Total synthesis of (±)-dendrobine by Roush's group (1978)

Scheme 18. Formal synthesis of (–)-dendrobine by Trost's group (1991)

Scheme 19. Total synthesis of (–)-dendrobine by Sha's group (1997)

Scheme 20. Total synthesis of (–)-dendrobine by Plietker's group (2018)

Scheme 21. Synthetic study of (–)-dendrobine by Heathcock's group (1975)

Scheme 22. Total synthesis of (–)-dendrobine by Carreira's group (2012)

Scheme 23. Synthetic study of (–)-dendrobine by Trauner's group (2018)

Figure 4. Overview of key reactions in the synthetic studies toward (±)-dendrobine

Figure 5. Overview of key recations in the synthetic research of (–)-dendrobine

研究组	年份	rac/(–)-Dendrobine	步骤数	总产率/%	参考文献
Yamada小组	1972	rac-Dendrobine	19	0.2	[9]
Inubushi小组	1972	rac-Dendrobine	15	0.2	[12]
Kende小组	1974	rac-Dendrobine	13	0.6	[8b]
Roush小组	1978	rac-Dendrobine	20	0.9	[14c]
研究组	年份	rac/(–)-Dendrobine	步骤数	总产率/%	参考文献
Livinghouse小组	1992	rac-Dendrobine	12	6.2	[11a]
Sha小组	1997	(–)-Dendrobine	15	1.6	[15b]
Carreira小组	2012	(–)-Dendrobine	16	7.6	[16b]
Plietker小组	2018	(–)-Dendrobine	12	6.7	[4e]

Table 1. Summary of total synthesis of dendrobine

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倍半萜生物碱Dendrobine的全合成研究进展

Advances on the Total Synthesis of Sesquiterpenoid Alkaloid Dendrobine

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