Literature DB >> 20446675

Approaches to N-methylwelwitindolinone C isothiocyanate: facile synthesis of the tetracyclic core.

Richard W Heidebrecht1, Brian Gulledge, Stephen F Martin.   

Abstract

The synthesis of a functionalized, tetracyclic core of N-methylwelwitindolinone C isothiocyanate is reported. The approach features a convergent coupling between an indole iminium ion and a highly functionalized vinylogous silyl ketene acetal followed by an intramolecular palladium-catalyzed cyclization that proceeds via an enolate arylation.

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Year:  2010        PMID： 20446675      PMCID： PMC2878383          DOI： 10.1021/ol1006373

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


  19 in total

1.  Bridgehead enolates and bridgehead alkenes in a welwistatin model series.

Authors:  Valerie Boissel; Nigel S Simpkins; Gurdip Bhalay; Alexander J Blake; William Lewis
Journal:  Chem Commun (Camb)       Date:  2009-01-21       Impact factor: 6.222

2.  An approach to the total synthesis of welwistatin.

Authors:  Thomas J Greshock; Raymond L Funk
Journal:  Org Lett       Date:  2006-06-08       Impact factor: 6.005

3.  Pd/P(t-Bu)(3): a mild and general catalyst for Stille reactions of aryl chlorides and aryl bromides.

Authors:  Adam F Littke; Lothar Schwarz; Gregory C Fu
Journal:  J Am Chem Soc       Date:  2002-06-05       Impact factor: 15.419

4.  Rapid access to the Welwitindolinone alkaloid skeleton by cyclization of indolecarboxaldehyde substituted cyclohexanones.

Authors:  Jérôme Baudoux; Alexander J Blake; Nigel S Simpkins
Journal:  Org Lett       Date:  2005-09-15       Impact factor: 6.005

5.  A general method for acylation of indoles at the 3-position with acyl chlorides in the presence of dialkylaluminum chloride.

Authors:  T Okauchi; M Itonaga; T Minami; T Owa; K Kitoh; H Yoshino
Journal:  Org Lett       Date:  2000-05-18       Impact factor: 6.005

6.  Total synthesis of (+/-)-welwitindolinone a isonitrile.

Authors:  Sarah E Reisman; Joseph M Ready; Atsushi Hasuoka; Catherine J Smith; John L Wood
Journal:  J Am Chem Soc       Date:  2006-02-08       Impact factor: 15.419

7.  Enantioselective total syntheses of welwitindolinone A and fischerindoles I and G.

Authors:  Phil S Baran; Jeremy M Richter
Journal:  J Am Chem Soc       Date:  2005-11-09       Impact factor: 15.419

8.  Synthesis of β-Heteroaryl Propionates via Trapping of Carbocations with π-Nucleophiles.

Authors:  Tsung-Hao Fu; Amy Bonaparte; Stephen F Martin
Journal:  Tetrahedron Lett       Date:  2009-07-01       Impact factor: 2.415

9.  Evolution of a synthetic strategy: total synthesis of (+/-)-welwitindolinone A isonitrile.

Authors:  Sarah E Reisman; Joseph M Ready; Matthew M Weiss; Atsushi Hasuoka; Makoto Hirata; Kazuhiko Tamaki; Timo V Ovaska; Catherine J Smith; John L Wood
Journal:  J Am Chem Soc       Date:  2008-01-17       Impact factor: 15.419

10.  Synthesis of fused 4,5-disubstituted indole ring systems by intramolecular friedel-crafts acylation of 4-substituted indoles.

Authors:  Eric Fillion; Aaron M Dumas
Journal:  J Org Chem       Date:  2008-03-06       Impact factor: 4.354
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  13 in total

1.  Total synthesis of (-)-N-methylwelwitindolinone C isothiocyanate.

Authors:  Alexander D Huters; Kyle W Quasdorf; Evan D Styduhar; Neil K Garg
Journal:  J Am Chem Soc       Date:  2011-08-11       Impact factor: 15.419

2.  Enantiospecific total synthesis of N-methylwelwitindolinone D isonitrile.

Authors:  Evan D Styduhar; Alexander D Huters; Nicholas A Weires; Neil K Garg
Journal:  Angew Chem Int Ed Engl       Date:  2013-10-02       Impact factor: 15.336

3.  Natural Products and Their Mimics as Targets of Opportunity for Discovery.

Authors:  Stephen F Martin
Journal:  J Org Chem       Date:  2017-09-15       Impact factor: 4.354

4.  Directed oxidative cyclizations to C2- or C4-positions of indole: efficient construction of the bicyclo[4.3.1]decane core of welwitindolinones.

Authors:  Vikram Bhat; James A Mackay; Viresh H Rawal
Journal:  Org Lett       Date:  2011-05-26       Impact factor: 6.005

5.  Total synthesis of N-methylwelwitindolinone D isonitrile.

Authors:  Vikram Bhat; Kevin M Allan; Viresh H Rawal
Journal:  J Am Chem Soc       Date:  2011-03-29       Impact factor: 15.419

6.  Total synthesis of oxidized welwitindolinones and (-)-N-methylwelwitindolinone C isonitrile.

Authors:  Kyle W Quasdorf; Alexander D Huters; Michael W Lodewyk; Dean J Tantillo; Neil K Garg
Journal:  J Am Chem Soc       Date:  2012-01-11       Impact factor: 15.419

7.  Synthesis of functionalized cyclohexenone core of welwitindolinones via rhodium-catalyzed [5 + 1] cycloaddition.

Authors:  Min Zhang; Weiping Tang
Journal:  Org Lett       Date:  2012-07-11       Impact factor: 6.005

8.  Lessons Learned while Traversing the Welwitindolinone Alkaloids Obstacle Course.

Authors:  Vikram Bhat; James A Mackay; Viresh H Rawal
Journal:  Tetrahedron       Date:  2011-09-24       Impact factor: 2.457

9.  Formal syntheses of naturally occurring welwitindolinones.

Authors:  Tsung-hao Fu; William T McElroy; Mariam Shamszad; Stephen F Martin
Journal:  Org Lett       Date:  2012-07-25       Impact factor: 6.005

10.  Concise total synthesis of (±)-actinophyllic acid.

Authors:  Brett A Granger; Ivan T Jewett; Jeffrey D Butler; Stephen F Martin
Journal:  Tetrahedron       Date:  2014-07-08       Impact factor: 2.457
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