Synthesis of Strained γ-Lactams by Palladium(0)-Catalyzed C(sp3)-H Alkenylation and Application to Alkaloid Synthesis

被引：49
作者：
Holstein, Philipp M. [1 ]
Dallier, David [1 ,2 ]
Vantourout, Julien [1 ]
Shaya, Janah [1 ]
Millet, Anthony [1 ]
Baudoin, Olivier [1 ,2 ]
机构：
[1] Univ Lyon 1, CNRS UMR 5246, Inst Chim & Biochim Mol & Supramol, CPE Lyon, 43 Blvd 11 Novembre 1918, F-69622 Villeurbanne, France
[2] Univ Basel, Dept Chem, St Johanns Ring 19, CH-4056 Basel, Switzerland
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2016年 / 55卷 / 08期
关键词：
C-C coupling; C-H activation; natural products; nitrogen heterocycles; palladium; C-H ACTIVATION; INTRAMOLECULAR ALKANE ARYLATION; DELTA-CONICEINE; ASYMMETRIC-SYNTHESIS; FACILE SYNTHESIS; FUNCTIONALIZATION; INDOLINES; DERIVATIVES; ACCESS; BONDS;
D O I：
10.1002/anie.201511457
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A variety of strained alpha-alkylidene-gamma-lactams were synthesized by palladium(0)-catalyzed intramolecular C(sp(3))-H alkenylation from easily accessible acyclic and monocyclic bromoalkene precursors. These lactams are valuable intermediates for accessing various classes of mono- and bicylic alkaloids containing a pyrrolidine ring, as illustrated with the synthesis of an advanced model of the marine natural product plakoridineA and of the indolizidine alkaloid delta-coniceine.
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收藏
页码：2805 / 2809
页数：5
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