An Approach to the Synthesis of Tetrahydroisoquinoline Alkaloids by Alkene Hydroamination: Synthesis of Coralydine

被引:11
作者
Pouilhes, Annie [1 ]
Baltaze, Jean-Pierre [1 ]
Kouklovsky, Cyrille [1 ]
机构
[1] Univ Paris Sud, Inst Chim Mol & Mat Orsay, CNRS, UMR 8182, F-91405 Orsay, France
关键词
alkaloids; total synthesis; nitrogen; heterocycles; ASYMMETRIC-SYNTHESIS; ISOQUINOLINE ALKALOIDS; STRATEGY;
D O I
10.1055/s-0033-1339375
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The protoberberine alkaloid coralydine was synthesized in a short sequence by a strategy including an intramolecular alkene hydroamination as the key step, followed by a Pictet-Spengler cyclization.
引用
收藏
页码:1805 / 1808
页数:4
相关论文
共 50 条
[21]   A Flexible Approach to Grandisine Alkaloids: Total Synthesis of Grandisines B, D, and F [J].
Kurasaki, Haruaki ;
Okamoto, Iwao ;
Morita, Nobuyoshi ;
Tamura, Osamu .
CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (46) :12754-12763
[22]   The Enantioselective Total Synthesis of Bisquinolizidine Alkaloids: A Modular "Inside-Out" Approach [J].
Scharnagel, Dagmar ;
Goller, Jessica ;
Deibl, Nicklas ;
Milius, Wolfgang ;
Breuning, Matthias .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (09) :2432-2435
[23]   Total Synthesis of (-)-Quinocarcin by Gold(I)-Catalyzed Regioselective Hydroamination [J].
Chiba, Hiroaki ;
Oishi, Shinya ;
Fujii, Nobutaka ;
Ohno, Hiroaki .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (36) :9169-9172
[24]   Synthesis of 2-epi-Pumiliotoxin C via a Challenging Intramolecular Hydroamination Key Step [J].
Lebrun, Marie-Eve ;
Pfeiffer, Jennifer Y. ;
Beauchemin, Andre M. .
SYNLETT, 2009, (07) :1087-1090
[25]   A Flexible Approach to the Synthesis of Type II and III Lepadin Alkaloids [J].
Hu, Yue ;
Gu, He ;
Jia, Yuanliang ;
Luo, Guiyin ;
Chen, Xiaochuan .
SYNTHESIS-STUTTGART, 2022, 54 (06) :1577-1586
[26]   Modular Approach in Synthesis of Polycyclic Indolizidine, Quinolizidine, and Related Alkaloids [J].
Kuntiyong, Punlop ;
Akkarasamiyo, Sunisa ;
Rayanil, Kanok-on .
CHEMISTRY-AN ASIAN JOURNAL, 2025,
[27]   Asymmetric Synthesis of Crispine A: Constructing Tetrahydroisoquinoline Scaffolds Using Pummerer Cyclizations [J].
Rotte, Sateesh Chandra Kumar ;
Chittiboyina, Amar G. ;
Khan, Ikhlas A. .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2013 (28) :6355-6360
[28]   Radical-initiated cyclization as a key step for the synthesis of oxoprotoberberine alkaloids [J].
Lee, Chih-Shone ;
Yu, Tsung-Ching ;
Luo, Jian-Wen ;
Cheng, Yen-Yao ;
Chuang, Che-Ping .
TETRAHEDRON LETTERS, 2009, 50 (31) :4558-4562
[29]   Synthesis of the sedum and related alkaloids: A personal perspective [J].
Bates, Roderick W. .
TETRAHEDRON LETTERS, 2018, 59 (07) :559-567
[30]   Synthesis of Atisine, Ajaconine, Denudatine, and Hetidine Diterpenoid Alkaloids by a Bioinspired Approach [J].
Li, Xiao-Huan ;
Zhu, Min ;
Wang, Zhi-Xiu ;
Liu, Xiao-Yu ;
Song, Hao ;
Zhang, Dan ;
Wang, Feng-Peng ;
Qin, Yong .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (50) :15667-15671