Literature DB >> 22235964

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

Kyle W Quasdorf1, Alexander D Huters, Michael W Lodewyk, Dean J Tantillo, Neil K Garg.   

Abstract

We report the total synthesis of (-)-N-methylwelwitindolinone C isonitrile, in addition to the total syntheses of the 3-hydroxylated welwitindolinones. Our routes to these elusive natural products feature the strategic use of a deuterium kinetic isotope effect to improve the efficiency of a late-stage nitrene insertion reaction. We also provide a computational prediction for the stereochemical configuration at C3 of the hydroxylated welwitindolinones, which was confirmed by experimental studies.
© 2011 American Chemical Society

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Year:  2012        PMID： 22235964      PMCID： PMC3266994          DOI： 10.1021/ja210837b

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  42 in total

1.  Catalytic asymmetric hydroxylation of oxindoles by molecular oxygen using a phase-transfer catalyst.

Authors:  Daisuke Sano; Kazuhiro Nagata; Takashi Itoh
Journal:  Org Lett       Date:  2008-03-19       Impact factor: 6.005

2.  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

3.  A stereoselective synthesis of (-)-tetrodotoxin.

Authors:  Andrew Hinman; J Du Bois
Journal:  J Am Chem Soc       Date:  2003-09-24       Impact factor: 15.419

4.  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

5.  Stereocontrolled synthesis of 20,21-dihydro N-methylwelwitindolinone B isothiocyanate.

Authors:  Vikram Bhat; Viresh H Rawal
Journal:  Chem Commun (Camb)       Date:  2011-07-27       Impact factor: 6.222

6.  Structure of the lycorinine alkaloid nobilisitine A.

Authors:  Brett D Schwartz; Lorenzo V White; Martin G Banwell; Anthony C Willis
Journal:  J Org Chem       Date:  2011-09-27       Impact factor: 4.354

7.  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

8.  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

9.  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

10.  Palladium-catalyzed alpha-arylation of oxindoles.

Authors:  Matthew J Durbin; Michael C Willis
Journal:  Org Lett       Date:  2008-03-06       Impact factor: 6.005
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  25 in total

1.  Total synthesis: Welwitindolinone is well worth it.

Authors:  John L Wood
Journal:  Nat Chem       Date:  2012-04-23       Impact factor: 24.427

2.  Synthesis of 2-D-L-Tryptophan by Sequential Ir-Catalyzed Reactions.

Authors:  Ravikrishna Vallakati; Abel T Plotnikov; Ryan A Altman
Journal:  Tetrahedron       Date:  2019-02-26       Impact factor: 2.457

3.  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

4.  Computational predictions of substituted benzyne and indolyne regioselectivities.

Authors:  Elias Picazo; K N Houk; Neil K Garg
Journal:  Tetrahedron Lett       Date:  2015-06-03       Impact factor: 2.415

5.  Identification and characterization of a welwitindolinone alkaloid biosynthetic gene cluster in the stigonematalean Cyanobacterium Hapalosiphon welwitschii.

Authors:  Matthew L Hillwig; Heather A Fuhrman; Kuljira Ittiamornkul; Tyler J Sevco; Daniel H Kwak; Xinyu Liu
Journal:  Chembiochem       Date:  2014-03-21       Impact factor: 3.164

6.  Catalytic Enantioselective Dihalogenation and the Selective Synthesis of (-)-Deschloromytilipin A and (-)-Danicalipin A.

Authors:  Matthew L Landry; Dennis X Hu; Grace M McKenna; Noah Z Burns
Journal:  J Am Chem Soc       Date:  2016-04-08       Impact factor: 15.419

7.  Expanding the Strained Alkyne Toolbox: Generation and Utility of Oxygen-Containing Strained Alkynes.

Authors:  Tejas K Shah; Jose M Medina; Neil K Garg
Journal:  J Am Chem Soc       Date:  2016-03-29       Impact factor: 15.419

8.  Harnessing the biocatalytic potential of iron- and α-ketoglutarate-dependent dioxygenases in natural product total synthesis.

Authors:  Christian R Zwick; Hans Renata
Journal:  Nat Prod Rep       Date:  2020-02-14       Impact factor: 13.423

9.  Using quantum chemical computations of NMR chemical shifts to assign relative configurations of terpenes from an engineered Streptomyces host.

Authors:  Q Nhu N Nguyen; Dean J Tantillo
Journal:  J Antibiot (Tokyo)       Date:  2016-05-18       Impact factor: 2.649

10.  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
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