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Literature DB >> 22593605

Pt-catalyzed cyclization/migration of propargylic alcohols for the synthesis of 3(2H)-furanones, pyrrolones, indolizines, and indolizinones.

Eric M Bunnelle¹, Cameron R Smith, Sharon K Lee, Surendra W Singaram, Allison J Rhodes, Richmond Sarpong.

Abstract

Several heterocycles such as furanones, pyrrolones, and indolizines, which are of pharmacological importance, are easily accessed via the Pt(II)-catalyzed heterocyclization/1,2-migration of propargylic ketols or hydroxy imine derivatives. This method sidesteps the challenges of traditional heteroaromatic oxygenation strategies such as regioselectivity and functional group tolerance in the syntheses of these heterocycles.

Entities: Chemical

Year: 2008 PMID： 22593605 PMCID： PMC3351138 DOI： 10.1016/j.tet.2008.02.103

Source DB: PubMed Journal: Tetrahedron ISSN： 0040-4020 Impact factor: 2.457

23 in total

1. Asymmetric alkynylation of aldehydes catalyzed by an In(III)/BINOL complex.

Authors: Ryo Takita; Kenichiro Yakura; Takashi Ohshima; Masakatsu Shibasaki
Journal: J Am Chem Soc Date: 2005-10-12 Impact factor: 15.419

2. Gold-catalyzed 1,2-migration of silicon, tin, and germanium en route to C-2 substituted fused pyrrole-containing heterocycles.

Authors: Ilya V Seregin; Vladimir Gevorgyan
Journal: J Am Chem Soc Date: 2006-09-20 Impact factor: 15.419

3. Gold(III)- and platinum(II)-catalyzed domino reaction consisting of heterocyclization and 1,2-migration: efficient synthesis of highly substituted 3(2H)-furanones.

Authors: Stefan F Kirsch; Jörg T Binder; Clémence Liébert; Helge Menz
Journal: Angew Chem Int Ed Engl Date: 2006-09-04 Impact factor: 15.336

4. An improved synthesis of functionalized biphenyl-based phosphine ligands.

Authors: H Tomori; J M Fox; S L Buchwald
Journal: J Org Chem Date: 2000-08-25 Impact factor: 4.354

5. Pt-catalyzed pentannulations from in situ generated metallo-carbenoids utilizing propargylic esters.

Authors: B A Bhanu Prasad; Francis K Yoshimoto; Richmond Sarpong
Journal: J Am Chem Soc Date: 2005-09-14 Impact factor: 15.419

6. Direct synthesis of monofunctionalized indolizine derivatives bearing alkoxymethyl substituents at C-3 and their benzofused analogues.

Authors: Joseph Kaloko; Anthony Hayford
Journal: Org Lett Date: 2005-09-15 Impact factor: 6.005

7. A novel Cu-assisted cycloisomerization of alkynyl imines: efficient synthesis of pyrroles and pyrrole-containing heterocycles.

Authors: A V Kel'in; A W Sromek; V Gevorgyan
Journal: J Am Chem Soc Date: 2001-03-07 Impact factor: 15.419

8. Synthesis of highly functionalized furanones via aldol reaction of 3-silyloxyfurans.

Authors: Jeffrey D Winkler; Kyungsoo Oh; Sylvie M Asselin
Journal: Org Lett Date: 2005-02-03 Impact factor: 6.005

9. Cyclobutenes by platinum-catalyzed cycloisomerization reactions of enynes.

Authors: Alois Fürstner; Paul W Davies; Tobias Gress
Journal: J Am Chem Soc Date: 2005-06-15 Impact factor: 15.419

10. Gold-catalyzed highly efficient access to 3(2H)-furanones from 2-oxo-3-butynoates and related compounds.

Authors: Yuanhong Liu; Meina Liu; Shenghai Guo; Huamin Tu; Yebing Zhou; Hongjun Gao
Journal: Org Lett Date: 2006-08-03 Impact factor: 6.005

7 in total

1. Indolizinones as synthetic scaffolds: fundamental reactivity and the relay of stereochemical information.

Authors: Alison R Hardin Narayan; Richmond Sarpong
Journal: Org Biomol Chem Date: 2011-11-09 Impact factor: 3.876

2. Remarkable facilitation of hetero-cycloisomerizations with water and other polar protic solvents: metal-free synthesis of indolizines.

Authors: Alison R Hardin Narayan; Richmond Sarpong
Journal: Green Chem Date: 2010 Impact factor: 10.182

3. Lanthanum tricyanide-catalyzed acyl silane-ketone benzoin additions and kinetic resolution of resultant alpha-silyloxyketones.

Authors: James C Tarr; Jeffrey S Johnson
Journal: J Org Chem Date: 2010-05-21 Impact factor: 4.354

4. Protic-solvent-mediated cycloisomerization of quinoline and isoquinoline propargylic alcohols: syntheses of (±)-3-demethoxyerythratidinone and (±)-cocculidine.

Authors: Stephen T Heller; Toshihiro Kiho; Alison R H Narayan; Richmond Sarpong
Journal: Angew Chem Int Ed Engl Date: 2013-09-05 Impact factor: 15.336