Synthesis of Strained γ-Lactams by Palladium(0)-Catalyzed C(sp(3) )-H Alkenylation and Application to Alkaloid Synthesis

Angewandte Chemie
Philipp M HolsteinOlivier Baudoin

Abstract

A variety of strained α-alkylidene-γ-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 plakoridine A and of the indolizidine alkaloid δ-coniceine.

References

Nov 10, 2000·Natural Product Reports·D O'Hagan
Aug 4, 2001·The Journal of Organic Chemistry·M O RasmussenA E Greene
Dec 9, 2003·Angewandte Chemie·Olivier BaudoinFrançoise Guéritte
Apr 26, 2006·Angewandte Chemie·Hongjun Ren, Paul Knochel
Nov 8, 2007·Journal of the American Chemical Society·Marc LafranceKeith Fagnou
Feb 6, 2008·Natural Product Reports·Joseph P Michael
Oct 22, 2008·Journal of the American Chemical Society·Manon ChaumontetOlivier Baudoin
Feb 10, 2010·Chemistry : a European Journal·Rodolphe JazzarOlivier Baudoin
Aug 5, 2010·Journal of the American Chemical Society·Sophie RousseauxOlivier Baudoin
Nov 3, 2010·Natural Product Reports·Ronaldo Aloise PilliMaria da Conceição Ferreira de Oliveira
Apr 21, 2011·Chemical Society Reviews·Olivier Baudoin
Sep 20, 2011·Chemical Communications : Chem Comm·Saithalavi AnasHenri B Kagan
Mar 13, 2012·Chemistry : a European Journal·Nicolas MartinOlivier Baudoin
Jul 6, 2014·Angewandte Chemie·Julia PedroniNicolai Cramer
Aug 27, 2014·Natural Product Reports·Jeremy Robertson, Kiri Stevens
Jun 3, 2015·Chemistry : a European Journal·David DaillerOlivier Baudoin
Aug 15, 2015·Angewandte Chemie·Julia Pedroni, Nicolai Cramer

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Citations

Nov 22, 2016·Chemistry : a European Journal·Josephin M HolsteinAndrea Rentmeister
May 17, 2017·Angewandte Chemie·David DaillerOlivier Baudoin
Feb 20, 2018·Chemical Communications : Chem Comm·Zaifeng YuanChengfeng Xia
Apr 29, 2016·Chemistry : a European Journal·Satoshi SuetsuguYoshiji Takemoto
Apr 5, 2017·Accounts of Chemical Research·Olivier Baudoin
Jul 20, 2019·The Journal of Organic Chemistry·Romain MelotOlivier Baudoin
Jul 13, 2017·Chemical Reviews·Jian HeJin-Quan Yu

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