Palladium-catalyzed glycosylation: novel synthetic approach to diverse N-heterocyclic glycosides

Organic Letters
Li JiXue-Wei Liu

Abstract

An efficient and highly stereoselective method for the construction of N-heterocyclic glycosides is reported. This method is based on a palladium-catalyzed allylation which proceeded to provide N-heterocyclic glycosyl compounds in good-to-excellent yields with β- or α-selectivity. Various N-nucleophiles were examined for this reaction and selected N-glycosyl isatin substrates were further elaborated to bis-indole sugars which have potential as antiproliferative drugs.

References

Jan 1, 1994·Advances in Carbohydrate Chemistry and Biochemistry·R R Schmidt, W Kinzy
Nov 7, 2003·Organic Letters·Pedro A Colinas, Rodolfo D Bravo
Feb 5, 2004·Journal of the American Chemical Society·Hahn KimChulbom Lee
Nov 19, 2004·Organic Letters·Yi HeLaura L Kiessling
Jun 28, 2005·Bioorganic & Medicinal Chemistry Letters·Lauren L Rossi, Amit Basu
Dec 7, 2005·European Journal of Medicinal Chemistry·Mathieu SassatelliPascale Moreau
Jan 18, 2006·Organic Letters·Sanjeeva R GuppiGeorge A O'Doherty
Jul 10, 2007·Organic Letters·Brandon P SchuffHien M Nguyen
Aug 4, 2007·Carbohydrate Research·Pedro A Colinas, Rodolfo D Bravo
Feb 22, 2008·Current Topics in Medicinal Chemistry·Peter Norris
Oct 18, 2008·Bioorganic & Medicinal Chemistry Letters·Brendan L WilkinsonAntony J Fairbanks
Jul 1, 2010·Chemical Communications : Chem Comm·Yuki KanekoYuichi Kobayashi
Jul 28, 2010·Oncogene·J Stagg, M J Smyth
Feb 3, 2011·Beilstein Journal of Organic Chemistry·Carolin Fischer, Burkhard Koenig
Mar 10, 2011·Chemical Society Reviews·Chi-Ming CheJie-Sheng Huang
Jul 12, 2012·Journal of the American Chemical Society·Ravula Satheesh BabuGeorge A O'Doherty
Nov 22, 2012·Journal of the American Chemical Society·Jagodige P Yasomanee, Alexei V Demchenko
Oct 11, 2013·Chemistry : a European Journal·Shaohua XiangXue-Wei Liu
Mar 15, 2014·Chemical Communications : Chem Comm·Shaohua XiangXue-Wei Liu

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Citations

May 27, 2015·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Ana M GomezJ Cristobal Lopez
Oct 26, 2016·ChemistryOpen·Rituparna Das, Balaram Mukhopadhyay
Jun 25, 2021·Chemical Science·Kumar Bhaskar PalXue-Wei Liu
May 14, 2020·The Journal of Organic Chemistry·Ying WangKun Zou
Feb 23, 2018·Accounts of Chemical Research·Wei-Lin LengXue-Wei Liu

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