Literature DB >> 23829389

Synthesis of spirocyclic indolines by interruption of the Bischler-Napieralski reaction.

Jonathan William Medley1, Mohammad Movassaghi.   

Abstract

The development of a versatile method for the synthesis of spirocyclic pyrrolidinoindolines is discussed. Treatment of N-acyltryptamines with trifluoromethanesulfonic anhydride-2-chloropyridine reagent combination affords highly persistent spiroindoleninium ions that are subject to intra- and intermolecular addition at C2 by nucleophiles.

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Year:  2013        PMID： 23829389      PMCID： PMC3779471          DOI： 10.1021/ol401465y

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  14 in total

1.  Novel and selective spiroindoline-based inhibitors of Sky kinase.

Authors:  Noel A Powell; Jeffrey T Kohrt; Kevin J Filipski; Michael Kaufman; Derek Sheehan; Jeremy E Edmunds; Amy Delaney; Yuli Wang; Francis Bourbonais; Doh-Yeel Lee; Frank Schwende; Fang Sun; Pat McConnell; Cornel Catana; Huifen Chen; Jeff Ohren; Lisa A Perrin
Journal:  Bioorg Med Chem Lett       Date:  2011-11-16       Impact factor: 2.823

Review 2.  Controlled microwave heating in modern organic synthesis.

Authors:  C Oliver Kappe
Journal:  Angew Chem Int Ed Engl       Date:  2004-11-26       Impact factor: 15.336

3.  Direct synthesis of pyridine derivatives.

Authors:  Mohammad Movassaghi; Matthew D Hill; Omar K Ahmad
Journal:  J Am Chem Soc       Date:  2007-07-31       Impact factor: 15.419

4.  Total synthesis of (+)-aspidospermidine: a new strategy for the enantiospecific synthesis of aspidosperma alkaloids.

Authors:  Joseph P Marino; Maria B Rubio; Ganfeng Cao; Alfonso de Dios
Journal:  J Am Chem Soc       Date:  2002-11-13       Impact factor: 15.419

5.  Direct Synthesis of Azaheterocycles from N-Aryl/Vinyl Amides. Synthesis of 4-(Methylthio)-2-phenylquinazoline and 4-(4-Methoxyphenyl)-2-phenylquinoline.

Authors:  Omar K Ahmad; Jonathan William Medley; Alexis Coste; Mohammad Movassaghi; Hiromi Kaise; Tohru Fukuyama
Journal:  Organic Synth       Date:  2012

6.  Asymmetric total synthesis of vindorosine, vindoline, and key vinblastine analogues.

Authors:  Yoshikazu Sasaki; Daisuke Kato; Dale L Boger
Journal:  J Am Chem Soc       Date:  2010-09-29       Impact factor: 15.419

7.  An efficient approach to Aspidosperma alkaloids via [4 + 2] cycloadditions of aminosiloxydienes: stereocontrolled total synthesis of (+/-)-tabersonine. Gram-scale catalytic asymmetric syntheses of (+)-tabersonine and (+)-16-methoxytabersonine. Asymmetric syntheses of (+)-aspidospermidine and (-)-quebrachamine.

Authors:  Sergey A Kozmin; Tetsuo Iwama; Yong Huang; Viresh H Rawal
Journal:  J Am Chem Soc       Date:  2002-05-01       Impact factor: 15.419

8.  The total synthesis of (plus or minus)-vindorosine.

Authors:  G Büchi; K E Matsumoto; H Nishimura
Journal:  J Am Chem Soc       Date:  1971-06-30       Impact factor: 15.419

9.  A versatile cyclodehydration reaction for the synthesis of isoquinoline and beta-carboline derivatives.

Authors:  Mohammad Movassaghi; Matthew D Hill
Journal:  Org Lett       Date:  2008-07-19       Impact factor: 6.005

10.  Enantioselective spirocyclizations from tryptophanol-derived oxazolopiperidone lactams.

Authors:  Mercedes Amat; Maria M M Santos; Antonia M Gómez; Danica Jokic; Elies Molins; Joan Bosch
Journal:  Org Lett       Date:  2007-06-29       Impact factor: 6.005
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  9 in total

1.  Electrophilic Carbonyl Activation: Competing Condensative Cyclizations of Tryptamine Derivatives.

Authors:  Fan Liu; Mohammad Movassaghi
Journal:  Tetrahedron Lett       Date:  2015-06-03       Impact factor: 2.415

2.  Direct Observation of Intermediates Involved in the Interruption of the Bischler-Napieralski Reaction.

Authors:  Kolby L White; Marius Mewald; Mohammad Movassaghi
Journal:  J Org Chem       Date:  2015-07-22       Impact factor: 4.354

3.  Enantioselective Total Synthesis of (-)-Deoxoapodine.

Authors:  Taek Kang; Kolby L White; Tyler J Mann; Amir H Hoveyda; Mohammad Movassaghi
Journal:  Angew Chem Int Ed Engl       Date:  2017-09-27       Impact factor: 15.336

4.  Concise and enantioselective total synthesis of (-)-mehranine, (-)-methylenebismehranine, and related Aspidosperma alkaloids.

Authors:  Marius Mewald; Jonathan William Medley; Mohammad Movassaghi
Journal:  Angew Chem Int Ed Engl       Date:  2014-09-04       Impact factor: 15.336

5.  Enantioselective Synthesis of (-)-Vallesine: Late-Stage C17-Oxidation via Complex Indole Boronation.

Authors:  Alyssa H Antropow; Nicholas R Garcia; Kolby L White; Mohammad Movassaghi
Journal:  Org Lett       Date:  2018-06-04       Impact factor: 6.005

6.  Concise Total Syntheses of (+)-Haplocidine and (+)-Haplocine via Late-Stage Oxidation of (+)-Fendleridine Derivatives.

Authors:  Kolby L White; Mohammad Movassaghi
Journal:  J Am Chem Soc       Date:  2016-08-26       Impact factor: 15.419

7.  C7-derivatization of C3-alkylindoles including tryptophans and tryptamines.

Authors:  Richard P Loach; Owen S Fenton; Kazuma Amaike; Dustin S Siegel; Erhan Ozkal; Mohammad Movassaghi
Journal:  J Org Chem       Date:  2014-11-10       Impact factor: 4.354

8.  Chemoselective α-Sulfidation of Amides Using Sulfoxide Reagents.

Authors:  Mario Leypold; Kyan A D'Angelo; Mohammad Movassaghi
Journal:  Org Lett       Date:  2020-10-13       Impact factor: 6.005

9.  Chemoselective γ-Oxidation of β,γ-Unsaturated Amides with TEMPO.

Authors:  Sebastian Heindl; Margaux Riomet; Ján Matyasovsky; Miran Lemmerer; Nicolas Malzer; Nuno Maulide
Journal:  Angew Chem Int Ed Engl       Date:  2021-07-20       Impact factor: 15.336
  9 in total

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