Synthesis of deoxyelephantopin analogues

The Journal of Antibiotics
Roman LagoutteNicolas Winssinger

Abstract

Deoxyelephantopin is a sesquiterpene lactone that was reported to be as effective in the treatment of mammary tumours and lung metastasis as taxol based on a murine orthotopic cancer model. Its germacrene skeleton harbours three Michael acceptors that can potentially engage a target covalently. Its strained 10-membered ring is densely functionalised and represents an important synthetic challenge. We herein describe our studies towards deoxyelephantopins using a ring-closing metathesis approach and report some unexpected observations.

References

Feb 15, 2001·Accounts of Chemical Research·T M Trnka, R H Grubbs
Aug 19, 2004·Journal of the American Chemical Society·Thomas R HoyeHongyu Zhao
Sep 24, 2004·Journal of the American Chemical Society·Hiromichi FujiokaYasuyuki Kita
Nov 19, 2004·Angewandte Chemie·Patricio E RomeroRobert McDonald
Jul 9, 2005·Angewandte Chemie·K C NicolaouDavid Sarlah
Sep 9, 2005·Angewandte Chemie·Carmen DrahlErik J Sorensen
Oct 14, 2005·Journal of the American Chemical Society·Arnab K ChatterjeeRobert H Grubbs
Aug 7, 2007·Angewandte Chemie·Pierre-Yves DakasNicolas Winssinger
Jan 28, 2009·Nature Structural & Molecular Biology·Toshimasa ItohJohn W R Schwabe
Feb 11, 2009·Journal of Medicinal Chemistry·Michele H Potashman, Mark E Duggan
Oct 13, 2009·Chemistry : a European Journal·Pierre-Yves DakasNicolas Winssinger
Nov 26, 2009·Journal of the American Chemical Society·Barry M TrostThomas Schmidt
Nov 26, 2009·Angewandte Chemie·Russell R A KitsonRichard J K Taylor
Jul 14, 2010·Chembiochem : a European Journal of Chemical Biology·Sofia BarluengaNicolas Winssinger
Oct 12, 2010·The Journal of Organic Chemistry·Thomas R HoyeHongyu Zhao
May 13, 2011·Current Drug Targets·Irmgard Merfort
Dec 1, 2011·Chemistry : a European Journal·Anne-Caroline ChanyNicolas Blanchard
Jun 19, 2012·Angewandte Chemie·Jeremy FournierJanine Cossy
Aug 21, 2013·Chemistry : a European Journal·Michael L SchulteCraig W Lindsley
Nov 23, 2013·Organic & Biomolecular Chemistry·Vincent DuplanNicolas Winssinger
Aug 8, 2014·Journal of Medicinal Chemistry·Jing LongYue Chen
Mar 17, 2015·Angewandte Chemie·Jean-Pierre DaguerNicolas Winssinger
May 11, 2016·Current Medicinal Chemistry·Yulin RenA Douglas Kinghorn
May 25, 2016·Nature Chemistry·Tiago RodriguesGisbert Schneider
Aug 20, 2016·Angewandte Chemie·Thomas A Baillie
Aug 20, 2016·Nature Communications·Roman LagoutteNicolas Winssinger
May 4, 2017·Proceedings of the National Academy of Sciences of the United States of America·Cameron R PyeRoger G Linington

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Citations

Jan 27, 2021·International Journal of Molecular Sciences·Younghoon KimTaebo Sim

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