SIOC English
有机化学
高级检索

有机化学 >

2013 , Vol. 33 >Issue 06: 1186 - 1194

DOI: https://doi.org/10.6023/cjoc201303056

综述与进展

斯替宁碱的合成方法研究进展

  • 陈静波 ,
  • 陈景超 ,
  • 谢彦 ,
  • 刘娜娜 ,
  • 刘丹丹 ,
  • 张洪彬
展开
  • 云南大学自然资源药物化学教育部重点实验室 昆明 650091

收稿日期: 2013-03-31

  修回日期: 2013-05-21

  网络出版日期: 2013-05-24

基金资助

国家自然科学基金(Nos.21062029, 20562013及20925205)资助项目.

收起

Research Progress on the Synthesis of Stenine

  • Chen Jingbo ,
  • Chen Jingchao ,
  • Xie Yan ,
  • Liu Nana ,
  • Liu Dandan ,
  • Zhang Hongbin
Expand
  • Key Laboratory of Medicinal Chemistry for Natural Resources, Ministry of Education, Yunnan University, Kunming 650091

Received date: 2013-03-31

  Revised date: 2013-05-21

  Online published: 2013-05-24

Supported by

Project supported by the the National Natural Science Foudation of China (Nos.21062029, 20562013, 20925205).

Fold

摘要

具有1H-吡咯并[1,2-a]氮杂和多取代全氢吲哚结构的斯替宁碱是百部生物碱的代表性结构, 其多环结构和连续的七个手性中心对不对称合成化学极具挑战性.按斯替宁碱合成中使用的关键方法分类, 对斯替宁碱的合成研究进展进行了综述.

关键词： 斯替宁; 消旋合成; 不对称合成

本文引用格式

陈静波 , 陈景超 , 谢彦 , 刘娜娜 , 刘丹丹 , 张洪彬 . 斯替宁碱的合成方法研究进展[J]. 有机化学, 2013 , 33(06) : 1186 -1194 . DOI: 10.6023/cjoc201303056

Abstract

The alkaloid stenine which has a representative pyrrolo[1,2-a]azepine nucleus and a highly substituted perhydroindole ring system is unique among Stemona alkaloids.The polycyclic system and the seven contiguous stereogenic centers in (-)-stenine present a challenge for asymmetric organic synthesis.Progresses toward the synthesis of stenine are reviewed in terms of the key strategies employed.

Key words： stenine; racemic synthesis; asymmitric synthesis

参考文献

[1] For reviews, see: (a) Götz, M.; Strunz, G.M.In Alkaloids, Ed.: Wiesner, K., Butterworth, London, 1973, Vol.9, pp.143～160.(b) Lin, W.H.; Ye, Y.; Xu, R.S.J.Nat.Prod.1992, 55, 571.(c) Xu, R.S.Nat.Prod.Chem.2000, 21, 729.(d) Pilli, R.A.; Ferreira de Oliveira, M.C.Nat.Prod.Rep.2000, 17, 177.(e) Greger, H.Planta Med.2006, 72, 99.
[2] Götz, M.; Edwards, O.E.The Alkaloids, Ed.: Manske, R.H.F., Academic Press, New York, 1967, Vol.9, pp.545～550.
[3] (a) Chen, Y.C.; Hart, D.J.J.Org.Chem.1990, 55, 6236.(b) Chen, Y.C.; Hart, D.J.J.Org.Chem.1993, 58, 3840.
[4] (a) Wipf, P.; Kim, Y.; Goldstein, D.M.J.Am.Chem.Soc.1995, 117, 11106.(b) Goldstein, D.M.; Wipf, P.Tetrahedron Lett.1996, 37, 739.(c) Wipf, P.; Li, W.J.Org.Chem.1999, 64, 4576.
[5] Morimoto, Y.; Iwahashi, M.; Nishida, K.; Hayashi, Y.; Shirahama, H.Angew.Chem., Int.Ed.Engl.1996, 35, 904.
[6] Jung, S.H.; Lee, J.E.; Joo, H.J.; Kim, S.H.; Koh, H.Y.Bull.Korean Chem.Soc.2000, 21, 159.
[7] (a) Ginn, J.D.; Padwa, A.Org.Lett.2002, 4, 1515.(b) Ginn, J.D.; Padwa, A.J.Org.Chem.2005, 70, 5197.
[8] Zeng, Y.; Reddy, D.S.; Hirt, E.; Aubé, J.Org.Lett.2004, 6, 4993.
[9] (a) Zeng, Y.; Aubé, J.J.Am.Chem.Soc.2005, 127, 15712.(b) Frankowski, K.J.; Golden, J.E.; Zeng, Y.; Lei, Y.; Aubé, J.J.Am.Chem.Soc.2008, 130, 6018.
[10] Zhu, L.; Lauchli, R.; Loo, M.; Shea, K.J.Org.Lett.2007, 9, 2269.
[11] Fujioka, H.; Nakahara, K.; Kotoku, N.; Ohba, Y.; Nagatomi, Y.; Wang, T.L.; Sawama, Y.; Murai, K.; Hirano, K.; Oki, T.; Wakamatsu, S.; Kita, Y.Chem.Eur.J.2012, 18, 13861.
[12] Chen, J.B.; Chen, J.C.; Xie, Y.; Zhang, H.B.Angew.Chem., Int.Ed.2012, 51, 1024.
[13] Boeckman, R.K.; Kamenecka, T.M.Jr.; Nelson, S.G.; Pruitt, J.R.; Barta, T.E.Tetrahedron Lett.1991, 32, 2581.
Options
文章导航

/

〈 〉