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2024 , Vol. 44 >Issue 6: 1793 - 1810

DOI: https://doi.org/10.6023/cjoc202309023

综述与进展

水鬼蕉碱Pancratistatin的合成方法研究进展

  • 梁蕾蕾 ,
  • 姚家灿 ,
  • 丁凡 ,
  • 徐畅 ,
  • 刘丹丹
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  • 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
†共同第一作者

收稿日期: 2023-11-28

  修回日期: 2024-01-12

  网络出版日期: 2024-03-05

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)

收起

Research Progress on the Synthetic Methods of Pancratistatin

  • Leilei Liang ,
  • Jiacan Yao ,
  • Fan Ding ,
  • Chang Xu ,
  • Dandan Liu
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  • 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
†These authors contributed equally to this work.
*

Received date: 2023-11-28

  Revised date: 2024-01-12

  Online published: 2024-03-05

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)

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摘要

水鬼蕉碱(Pancratistatin)是具有显著抗肿瘤活性的天然生物碱, 包含高度羟基化六元环的异喹诺酮骨架, 有6个连续的手性中心. 芳环上取代基的区域选择性引入、内酰胺环的高效构建以及六取代环己烷的立体控制性合成是其全合成的主要挑战. 综述了水鬼蕉碱的初次合成工作, 以及2000年以来的全合成研究进展, 对合成策略和反应关键步骤进行阐述.

关键词： 水鬼蕉碱; 消旋合成; 不对称合成

本文引用格式

梁蕾蕾 , 姚家灿 , 丁凡 , 徐畅 , 刘丹丹 . 水鬼蕉碱Pancratistatin的合成方法研究进展[J]. 有机化学, 2024 , 44(6) : 1793 -1810 . DOI: 10.6023/cjoc202309023

Abstract

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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