SIOC English
有机化学
高级检索

有机化学 >

2025 , Vol. 45 >Issue 3: 837 - 851

DOI: https://doi.org/10.6023/cjoc202410006

综述与进展

三环海洋生物碱Cylindricines/Lepadiformines/Fasicularin的合成进展

  • 李芸杉 ,
  • 张钰欣 ,
  • 唐叶峰
展开
  • a 清华大学药学院 北京生物结构前沿研究中心 生命有机磷化学及化学生物学教育部重点实验室 北京 100084
    b 重庆大学药学院 创新药物研究中心 重庆 401331

收稿日期: 2024-10-12

  修回日期: 2024-12-01

  网络出版日期: 2024-12-20

基金资助

国家自然科学基金(22271172); 国家自然科学基金(22471139)

收起

Recent Advance in the Synthesis of Tricyclic Marine Alkaloids: Cylindricines, Lepadiformines, and Fasicularin

  • Yunshan Li ,
  • Yuxin Zhang ,
  • Yefeng Tang
Expand
  • a MOE Key Laboratory of Bioorganic Phosphorus Chemistry and Chemical Biology, Beijing Advanced Innovation Center for Structural Biology, School of Pharmaceutical Sciences, Tsinghua University, Beijing 100084
    b Innovative Drug Research Center, School of Pharmaceutical Sciences, Chongqing University, Chongqing 401331
* E-mail:

Received date: 2024-10-12

  Revised date: 2024-12-01

  Online published: 2024-12-20

Supported by

National Natural Science Foundation of China(22271172); National Natural Science Foundation of China(22471139)

Fold

摘要

Cylindricines, lepadiformines和fasicularin是一系列具有氢化吡咯[2,1-j]喹啉(6/6/5)或氢化吡啶[2,1-j]喹啉(6/6/6)核心骨架的三环海洋生物碱. 该类天然产物具有新颖的化学结构和广泛的生物学活性, 近40年来吸引了众多合成化学家的研究兴趣. 综述了自2017年以来关于该类天然产物的合成研究进展, 对每个合成中的关键构环反应进行了分析和总结.

关键词： 生物碱; 海洋天然产物; 全合成

本文引用格式

李芸杉 , 张钰欣 , 唐叶峰 . 三环海洋生物碱Cylindricines/Lepadiformines/Fasicularin的合成进展[J]. 有机化学, 2025 , 45(3) : 837 -851 . DOI: 10.6023/cjoc202410006

Abstract

Cylindricines, lepadiformines and fasicularin consititute a small class of tricyclic marine alkaloids featuring a perhydropyrrolo[2,1-j]quinolines (6/6/5) or perhydropyrido[2,1-j]quinolines (6/6/6) core skeleton. These natural products possess novel chemical structures and exhibit a wide range of biological activities, thus attracting significant interest from synthetic chemists over the past four decades. The recent advance in the synthesis of this unique class of natural products since 2017 is summarized, focusing on the key steps that enable the assembly of their tricyclic skeletons.

Key words： alkaloid; marine natural product; total synthesis

参考文献

[1]
(a) Blackman, A. J.; Li, C.; Hockless, D. C. R.; Skelton, B. W.; White, A. H. Tetrahedron 1993, 49, 8645.
[1]
(b) Biard, J. F.; Guyot, S.; Roussakis, C.; Verbist, J. F.; Vercauteren, J.; Weber, J. F.; Boukef, K. Tetrahedron Lett. 1994, 35, 2691.
[1]
(c) Li, C. P.; Blackman, A. J. Aust. J. Chem. 1994, 47, 1355.
[1]
(d) Li, C. P.; Blackman, A. J. Aust. J. Chem. 1995, 48, 955.
[1]
(e) Patil, A. D.; Freyer, A. J.; Reichwein, R.; Carte, B.; Killmer, L. B.; Faucette, L.; Johnson, R. K.; Faulkner, D. J. Tetrahedron Lett. 1997, 38, 363.
[2]
(a) Jugé, M.; Grimaud, N.; Biard, J.-F.; Sauviat, M.-P.; Nabil, M.; Verbist, J.-F.; Petit, J.-Y. Toxicon 2001, 39, 1231.
[2]
(b) Sauviat, M. P.; Vercauteren, J.; Grimaud, N.; Juge, M.; Nabil, M.; Petit, J. Y.; Biard, J. F. J. Nat. Prod. 2006, 69, 558.
[3]
Dutta, S.; Abe, H.; Aoyagi, S.; Kibayashi, C.; Gates, K. S. J. Am. Chem. Soc. 2005, 127, 15004.
[4]
Snider, B. B.; Liu, T. J. Org. Chem. 1997, 62, 5630.
[5]
Weinreb, S. M. Chem. Rev. 2006, 106, 2531.
[6]
Chiba, S.; Kaga, A. Synthesis 2017, 50, 685.
[7]
Wu, J.-L.; Chiou, W.-H. J. Org. Chem. 2020, 85, 9051.
[8]
Wang, Y.-T.; Wu, J.-L.; Chiou, W.-H. Org. Lett. 2022, 24, 5957.
[9]
Pastor, A.; Prinsloo, R.; Burford, K. N.; Macdonald, A. R.; Parvez, M.; Gendy, C.; Back, T. G. J. Org. Chem. 2023, 88, 13813.
[10]
Hiraoka, S.; Matsumoto, T.; Matsuzaka, K.; Sato, T.; Chida, N. Angew. Chem., Int. Ed. 2019, 58, 4381.
[11]
Yamamoto, S.; Komiya, Y.; Kobayashi, A.; Minamikawa, R.; Oishi, T.; Sato, T.; Chida, N. Org. Lett. 2019, 21, 1868.
[12]
Lin, H.-C.; Xie, P.-P.; Dai, Z.-Y.; Zhang, S.-Q.; Wang, P.-S.; Chen, Y.-G.; Wang, T.-C.; Hong, X.; Gong, L.-Z. J. Am. Chem. Soc. 2019, 141, 5824.
[13]
Takashima, K.; Hayakawa, D.; Gouda, H.; Toyooka, N. J. Org. Chem. 2019, 84, 5222.
[14]
Shimomura, M.; Sato, M.; Azuma, H.; Sakata, J.; Tokuyama, H. Org. Lett. 2020, 22, 3313.
[15]
Huang, Y.-H.; Liu, Z.-J.; Huang, P.-Q. Org. Chem. Front. 2022, 9, 58.
[16]
Piccichè, M.; Pinto, A.; Griera, R.; Bosch, J.; Amat, M. Org. Lett. 2022, 24, 5356.
[17]
(a) Yoshimura, A.; Hanzawa, R.; Fuwa, H. Org. Lett. 2022, 24, 6237.
[17]
(b) Hanzawa, R.; Fuwa, H. Org. Lett. 2023, 25, 1984.
[17]
(c) Takatori, Y.; Fuwa, H. J. Org. Chem. 2024, 89, 11693.
[18]
Dukes, D. M.; Atanassov, V. K.; Smith, J. M. Chem. Sci. 2024, 15, 16554.
[19]
Li, Y.; Zhang, J.; Chen, Y.; Pang, J.; Chen, Y.; Tang, Y. Angew. Chem., Int. Ed. 2024, e202414985.
Options
文章导航

/

〈 〉