Literature DB >> 24009078

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

Stephen T Heller1, Toshihiro Kiho, Alison R H Narayan, Richmond Sarpong.   

Abstract

Putting the "benz" in indolizinones: A cycloisomerization approach to benz[g]indolizinones and benz[e]indolizinones provides the first general route to these unique azacycles (see example). The utility of the benzindolizinone products was demonstrated by the application of this method to the total synthesis of the Erythrina alkaloids 3-demethoxyerythratidinone and cocculidine.
Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  Erythrina alkaloids; Schrock catalysts; cycloisomerization; heterocycles; molybdenum

Mesh：

Substances：

Year:  2013        PMID： 24009078      PMCID： PMC4000449          DOI： 10.1002/anie.201304687

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


  17 in total

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

Authors:  Eric M Bunnelle; Cameron R Smith; Sharon K Lee; Surendra W Singaram; Allison J Rhodes; Richmond Sarpong
Journal:  Tetrahedron       Date:  2008-02-28       Impact factor: 2.457

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.  Concise synthesis of the Erythrina alkaloid 3-demethoxyerythratidinone via combined rhodium catalysis.

Authors:  Jung Min Joo; Ramoncito A David; Yu Yuan; Chulbom Lee
Journal:  Org Lett       Date:  2010-11-19       Impact factor: 6.005

4.  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

5.  Quick access to druglike heterocycles: facile silver-catalyzed one-pot multicomponent synthesis of aminoindolizines.

Authors:  Yaguang Bai; Jing Zeng; Jimei Ma; Bala Kishan Gorityala; Xue-Wei Liu
Journal:  J Comb Chem       Date:  2010-09-13

6.  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

7.  New approaches for the synthesis of erythrinan alkaloids.

Authors:  Fengzhi Zhang; Nigel S Simpkins; Alexander J Blake
Journal:  Org Biomol Chem       Date:  2009-03-24       Impact factor: 3.876

8.  LiCl-mediated preparation of highly functionalized benzylic zinc chlorides.

Authors:  Albrecht Metzger; Matthias A Schade; Paul Knochel
Journal:  Org Lett       Date:  2008-02-21       Impact factor: 6.005

9.  Gold-catalyzed multicomponent synthesis of aminoindolizines from aldehydes, amines, and alkynes under solvent-free conditions or in water.

Authors:  Bin Yan; Yuanhong Liu
Journal:  Org Lett       Date:  2007-09-14       Impact factor: 6.005

10.  Synthesis of the erythrina alkaloid 3-demethoxyerythratidinone. Novel acid-induced rearrangements of its precursors.

Authors:  Qiu Wang; Albert Padwa
Journal:  Org Lett       Date:  2006-02-16       Impact factor: 6.005
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  10 in total

1.  Mechanistic Investigations of the Iron(III)-Catalyzed Carbonyl-Olefin Metathesis Reaction.

Authors:  Jacob R Ludwig; Susan Phan; Christopher C McAtee; Paul M Zimmerman; James J Devery; Corinna S Schindler
Journal:  J Am Chem Soc       Date:  2017-07-28       Impact factor: 15.419

2.  Lewis Acid Catalyzed Carbonyl-Olefin Metathesis.

Authors:  Jacob R Ludwig; Corinna S Schindler
Journal:  Synlett       Date:  2017       Impact factor: 2.454

3.  Iron(III)-catalysed carbonyl-olefin metathesis.

Authors:  Jacob R Ludwig; Paul M Zimmerman; Joseph B Gianino; Corinna S Schindler
Journal:  Nature       Date:  2016-04-27       Impact factor: 49.962

4.  Beyond olefins: new metathesis directions for synthesis.

Authors:  Marc R Becker; Rebecca B Watson; Corinna S Schindler
Journal:  Chem Soc Rev       Date:  2018-10-29       Impact factor: 54.564

5.  A Short Synthesis of (±)-3-Demethoxyerythratidinone by Ligand-Controlled Selective Heck Cyclization of Equilibrating Enamines.

Authors:  Emma E Blackham; Kevin I Booker-Milburn
Journal:  Angew Chem Int Ed Engl       Date:  2017-05-04       Impact factor: 15.336

6.  Copper-catalyzed condensation of imines and α-diazo-β-dicarbonyl compounds: modular and regiocontrolled synthesis of multisubstituted pyrroles.

Authors:  Wei Wen Tan; Naohiko Yoshikai
Journal:  Chem Sci       Date:  2015-08-03       Impact factor: 9.825

7.  Intramolecular azavinyl carbene-triggered rearrangement of furans.

Authors:  Anton S Makarov; Maxim G Uchuskin; A Stephen K Hashmi
Journal:  Chem Sci       Date:  2019-07-26       Impact factor: 9.825

8.  Brønsted-Acid-Catalyzed Intramolecular Carbonyl-Olefin Reactions: Interrupted Metathesis vs Carbonyl-Ene Reaction.

Authors:  Tanmay Malakar; Paul M Zimmerman
Journal:  J Org Chem       Date:  2021-01-21       Impact factor: 4.354

Review 9.  Carbonyl-Olefin Metathesis.

Authors:  Haley Albright; Ashlee J Davis; Jessica L Gomez-Lopez; Hannah L Vonesh; Phong K Quach; Tristan H Lambert; Corinna S Schindler
Journal:  Chem Rev       Date:  2021-06-16       Impact factor: 72.087

10.  Tropylium-promoted carbonyl-olefin metathesis reactions.

Authors:  Uyen P N Tran; Giulia Oss; Domenic P Pace; Junming Ho; Thanh V Nguyen
Journal:  Chem Sci       Date:  2018-05-04       Impact factor: 9.825
  10 in total

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