Total synthesis of (-)-(α)-kainic acid via a diastereoselective intramolecular [3 + 2] cycloaddition reaction of an aryl cyclopropyl ketone with an alkyne

Organic Letters
Zhi LuoYuanchao Li

Abstract

An enantioselective synthesis of (-)-(α)-kainic acid in 15 steps with an overall yield of 24% is reported. The pyrrolidine kainoid precursor with the required C2/C3 trans stereochemistry was prepared with complete diastereoselectivity via an unprecedented SmI2-catalyzed intramolecular [3 + 2] cycloaddition reaction of an aryl cyclopropyl ketone and an alkyne. Double bond isomerization was then employed to set the remaining stereochemistry at the C4 position en route to (-)-(α)-kainic acid.

References

Jan 1, 1994·Progress in Neurobiology·G Sperk
May 20, 1998·Natural Product Reports·M G Moloney
Sep 1, 1999·Natural Product Reports·M G Moloney
Feb 1, 1996·Chemical Reviews·Gary A. Molander, Christina R. Harris
Feb 19, 2002·Chemical Reviews·Alberto Brandi, Andrea Goti
Nov 15, 2002·Natural Product Reports·Mark G Moloney
Apr 10, 2003·Chemical Reviews·Hans-Ulrich Reissig, Reinhold Zimmer
Apr 10, 2003·Chemical Reviews·Alberto BrandiAndrea Goti
Jul 15, 2004·Chemical Reviews·David J EdmondsDavid J Procter
Mar 31, 2005·Journal of the American Chemical Society·Barry M Trost, Michael T Rudd
Nov 17, 2006·Organic Letters·Sushil K PandeyJean-François Poisson
Sep 1, 2007·Organic Letters·Lei Liu, John Montgomery
Jun 7, 2008·Accounts of Chemical Research·Guo-Qiang LinXing-Wen Sun
Jul 17, 2008·Angewandte Chemie·Veejendra K Yadav, Vardhineedi Sriramurthy
Apr 9, 2009·The Journal of Organic Chemistry·Mahesh S MajikSantosh G Tilve
Aug 29, 2009·Angewandte Chemie·K C NicolaouJason S Chen
Sep 1, 2009·Chemistry : a European Journal·Takashi TamakiSensuke Ogoshi
Feb 13, 2010·Organic Letters·Andreas Farwick, Günter Helmchen
Sep 25, 2010·The Journal of Organic Chemistry·Matthew J CampbellShanina D Sanders
Jan 11, 2011·Journal of the American Chemical Society·Zhan LuTehshik P Yoon
Mar 23, 2011·Organic Letters·Satoshi TakitaTohru Fukuyama
Apr 21, 2011·Organic Letters·Takuma KamonTakehiko Yoshimitsu
Aug 27, 2011·The Journal of Organic Chemistry·Guoqing WeiTheodore Cohen
Mar 17, 2012·Chemistry : a European Journal·Fides BenfattiJérôme Waser

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Citations

Nov 18, 2015·The Journal of Organic Chemistry·Ekaterina M BudyninaMikhail Ya Melnikov
Jan 22, 2015·Chemistry : a European Journal·Ming ZhangTakashi Ohshima
Apr 29, 2014·Organic & Biomolecular Chemistry·Xiang-Yin TianHenry N C Wong
Jul 20, 2016·Chemistry : a European Journal·Sophie RacineJérôme Waser
Feb 26, 2016·Chemical & Pharmaceutical Bulletin·Makoto InaiToshiyuki Kan
Jul 28, 2016·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Seung-Mann PaekHwayoung Yun
Mar 9, 2013·The Journal of Organic Chemistry·Naredla Kesava Reddy, Srivari Chandrasekhar
Apr 25, 2014·Chemical Reviews·Michal SzostakDavid J Procter
Apr 20, 2014·Organic Letters·Kentaro OeTetsuro Shinada
Mar 26, 2014·Organic Letters·Hitoshi OuchiToshiyuki Kan

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