Research Progress on the Synthetic Methods of Pancratistatin

doi:10.6023/cjoc202309023

Chinese Journal of Organic Chemistry ›› 2024, Vol. 44 ›› Issue (6): 1793-1810.DOI: 10.6023/cjoc202309023 Previous Articles Next Articles

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水鬼蕉碱Pancratistatin的合成方法研究进展

梁蕾蕾^b,†, 姚家灿^a,†, 丁凡^a, 徐畅^a, 刘丹丹^a^,^*()

a 昆明医科大学药学院暨云南省天然药物药理重点实验室昆明 650500
b 昆明医科大学基础医学院昆明 650500

收稿日期:2023-11-28 修回日期:2024-01-12 发布日期:2024-03-05
作者简介:
^†共同第一作者
基金资助:
国家自然科学基金(2104044); 云南省基础研究计划(202201AS070086); 云南省科技厅-昆明医科大学应用基础研究联合专项(202201AY070001-003); 云南省科技厅-昆明医科大学应用基础研究联合专项(202101AY070001-041); 云南省院士专家工作站(202305AF150054); 云南省天然药物药理重点实验室开放基金(YKLPNP-G2305)

Research Progress on the Synthetic Methods of Pancratistatin

Leilei Liang^b,†, Jiacan Yao^a,†, Fan Ding^a, Chang Xu^a, Dandan Liu^a,*()

a School of Pharmaceutical Sciences and Yunnan Key Laboratory of Pharmacology for Natural Products,Kunming Medical University, Kunming 650500
b Faculty of Basic Medical Science, Kunming Medical University, Kunming 650500

Received:2023-11-28 Revised:2024-01-12 Published:2024-03-05
Contact: * liudandan1017@qq.com
About author:
^†These authors contributed equally to this work.
Supported by:
National Natural Science Foundation of China(2104044); Yunnan Fundamental Research Projects(202201AS070086); Yunnan Provincial Science and Technology Department-Kunming Medical University Applied Basic Research Joint Special Fund Project(202201AY070001-003); Yunnan Provincial Science and Technology Department-Kunming Medical University Applied Basic Research Joint Special Fund Project(202101AY070001-041); Yunnan Academician Expert Workstation(202305AF150054); Open Fund of Yunnan Key Laboratory of Pharmacology for Natural Products(YKLPNP-G2305)

Pancratistatin is a natural alkaloid with prominent antitumor activity. Structurally, pancratistatin has an isocarbostyril core skeleton, fused with a highly oxygenated cyclohexane ring, with six consecutive stereogenic centers. Regioselective introduction of substituted aromatic ring into the core structure, construction of the lactam ring, and control of stereocenters are major challenges in the synthesis of pancratistatin. The preliminary synthetic work of pancratistatin and the research progresses of its total synthesis since 2000 are summarized, and the synthetic strategies and key steps during the total synthesis are illustrated.

Key words: pancratistatin, racemic synthesis, asymmetric synthesis

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Leilei Liang, Jiacan Yao, Fan Ding, Chang Xu, Dandan Liu. Research Progress on the Synthetic Methods of Pancratistatin[J]. Chinese Journal of Organic Chemistry, 2024, 44(6): 1793-1810.

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Fig. & Tab. 21

Figure 1. Selected amaryllidaceae alkaloids

Scheme 1. Synthesis of (±)-pancratistatin by Danishefsky’s group

Scheme 2. Synthesis of (±)-pancratistatin by Kim’s group

Scheme 3. Synthesis of (±)-pancratistatin by Cho’s group

Scheme 4. Synthesis of (±)-pancratistatin by Cho’s group

Scheme 5. Synthesis of (+)-pancratistatin by Rigby’s group

Scheme 6. Synthesis of (+)-narciclasine by Rigby’s group

Scheme 7. Synthesis of (+)-pancratistatin by Pettit’s group

Scheme 8. Synthesis of (+)-22 by Kim’s group

Scheme 9. Synthesis of (+)-pancratistatin by Li’s group

Scheme 10. Synthesis of (+)-pancratistatin by Medsen’s group

Scheme 11. Synthesis of (+)-pancratistatin by Alonso’s group

Scheme 12. Synthesis of (+)-pancratistatin by Sato’s group

Scheme 13. Synthesis of (+)-pancratistatin by Ellman’s group

Scheme 14. Synthesis of (+)-pancratistatin by Sarlah’s group

Scheme 15. Synthesis of (+)-narciclasine by Sarlah’s group

Scheme 16. Synthesis of key intermediate 145 by our group

Scheme 17. In situ 1H NMR monitoring intramolecular Henry of the reaction

Scheme 18. Energy profile of reaction 146 to 147

Scheme 19. Energy profile of transfomation 147b to 147a

Scheme 20. Synthesis of (+)-pancratistatin by our group

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水鬼蕉碱Pancratistatin的合成方法研究进展

Research Progress on the Synthetic Methods of Pancratistatin

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