Recent Progress in the Total Synthesis of Daphniphyllum Alkaloids

doi:10.6023/cjoc202409017

Chinese Journal of Organic Chemistry ›› 2025, Vol. 45 ›› Issue (3): 866-880.DOI: 10.6023/cjoc202409017 Previous Articles Next Articles

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虎皮楠生物碱全合成研究进展

毛海康^a^,^b, 徐晶^b^,^*()

a 哈尔滨工业大学化工与化学学院哈尔滨 150001
b 南方科技大学化学系深圳格拉布斯研究院广东省催化化学重点实验室深圳市小分子药物发现与合成重点实验室广东深圳 518055

收稿日期:2024-09-16 修回日期:2024-10-31 发布日期:2024-12-19
基金资助:
国家自然科学基金(22271136); 国家自然科学基金(22471117); 深圳市科技创新委员会(JCYJ20220814203252001); 深圳市小分子药物发现与合成重点实验室(ZDSYS20190902093215877); 广东省催化化学重点实验室(2020B121201002); 广东省创新团队(2019BT02Y335); 广东省教育厅高校基础研究重大项目(2021ZDZX2035); 广东省普通高校创新团队(2020KCXTD016)

Recent Progress in the Total Synthesis of Daphniphyllum Alkaloids

Haikang Mao^a^,^b, Jing Xu^b()

a School of Chemistry and Chemical Engineering, Harbin Institute of Technology, Harbin 150001
b Shenzhen Key Laboratory of Small Molecule Drug Discovery and Synthesis, Guangdong Provincial Key Laboratory of Catalysis, Shenzhen Grubbs Institute, Department of Chemistry, Southern University of Science and Technology, Shenzhen, Guangdong 518055

Received:2024-09-16 Revised:2024-10-31 Published:2024-12-19
Contact: * E-mail: xuj@sustech.edu.cn
Supported by:
National Natural Science Foundation of China(22271136); National Natural Science Foundation of China(22471117); Shenzhen Science, Technology and Innovation Commission(JCYJ20220814203252001); Shenzhen Key Laboratory of Small Molecule Drug Discovery and Synthesis(ZDSYS20190902093215877); Guangdong Provincial Key Laboratory of Catalysis(2020B121201002); Guangdong Innovative Program(2019BT02Y335); Education Department of Guangdong Province, Key Research Projects in Colleges and Universities in Guangdong Province(2021ZDZX2035); Innovative Team of Universities in Guangdong Province(2020KCXTD016)

Since the isolation of the first member in 1909, over 300 Daphniphyllum alkaloids have been isolated to date. These Daphniphyllum alkaloids have attracted the attention of many organic chemists due to their wide range of biological activities and complex, diverse and polycyclic skeletal structures. So far, more than 40 Daphniphyllum alkaloids have been synthesized. In this review, the research works of different research groups on the total synthesis of 27 Daphniphyllum alkaloids since 2021 are summarized.

Key words: total synthesis, natural products, Daphniphyllum alkaloids, synthetic strategies

Cite this article

Haikang Mao, Jing Xu. Recent Progress in the Total Synthesis of Daphniphyllum Alkaloids[J]. Chinese Journal of Organic Chemistry, 2025, 45(3): 866-880.

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Fig. & Tab. 16

Scheme 1. Total synthesis of (–)-daphenylline and (–)-himalensine A by the Qiu group

Scheme 2. Total synthesis of (–)-daphenylline by the Lu group

Scheme 3. Total synthesis II of (–)-daphenylline by the Lu group

Scheme 4. Total synthesis of daphgraciline by the Li group

Scheme 5. Total synthesis of daphnillonin B by the Li group

Scheme 6. Total synthesis of (–)-10-deoxydaphnipaxianine A、(+)-daphlongamine E and (+)-calyciphylline R by the Xu group

Scheme 7. Total synthesis of daphnezomine L methyl ester and calyciphylline K by the Xu group

Scheme 8. Total synthesis of caldaphnidine D by the Xu group

Scheme 9. Total synthesis of (–)-himalensine A by the Dixon group

Scheme 10. Total synthesis of (–)-daphnezomine A、(–)-daphnezomine B and (+)-dapholdhamine B by the Zhai group

Scheme 11. Total synthesis of calyciphylline A-type Daphniphyllum alkaloids by the Li group

Scheme 12. Total synthesis of macrodaphniphyllamine-type Daphniphyllum alkaloids by the Li group

Scheme 13. Total synthesis of daphnilongeranin A-type Daphniphyllum alkaloids by the Li group

Scheme 14. Total synthesis of daphnicyclidin D-type Daphniphyllum alkaloids by the Li group

Scheme 15. Total synthesis of (–)-daphenylline by the Yang group

Scheme 16. Total synthesis of daphenylline by the Sarpong group

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虎皮楠生物碱全合成研究进展

Recent Progress in the Total Synthesis of Daphniphyllum Alkaloids

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