Literature DB >> 20733933

Welwitindolinone C synthetic studies. Construction of the welwitindolinone carbon skeleton via a transannular nitrone cycloaddition.

David B Freeman1, Alexandra A Holubec, Matthew W Weiss, Julie A Dixon, Akio Kakefuda, Masami Ohtsuka, Munenori Inoue, Rishi G Vaswani, Hidenori Ohki, Brian D Doan, Sarah E Reisman, Brian M Stoltz, Joshua J Day, Ran N Tao, Noah A Dieterich, John L Wood.   

Abstract

Described is the construction of the N-methylwelwitindolinone C core via an efficient strategy that employs a sequential rhodium carbenoid-mediated O-H insertion, Claisen rearrangement and transannular [3+2] nitrone cycloaddition.

Entities:  

Year:  2010        PMID： 20733933      PMCID： PMC2924776          DOI： 10.1016/j.tet.2010.04.131

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


  22 in total

1.  Microwave-assisted synthesis of isonitriles: a general simple methodology.

Authors:  Andrea Porcheddu; Giampaolo Giacomelli; Margherita Salaris
Journal:  J Org Chem       Date:  2005-03-18       Impact factor: 4.354

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.  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

4.  Efficient synthesis of 1alpha-fluoro A-ring phosphine oxide, a useful building block for vitamin D analogues, from (S)-carvone via a highly selective palladium-catalyzed isomerization of dieneoxide to dieneol.

Authors:  M M Kabat; L M Garofalo; A R Daniewski; S D Hutchings; W Liu; M Okabe; R Radinov; Y Zhou
Journal:  J Org Chem       Date:  2001-09-07       Impact factor: 4.354

5.  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

6.  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

7.  A synthesis of the welwistatin core.

Authors:  Ryan Lauchli; Kenneth J Shea
Journal:  Org Lett       Date:  2006-11-09       Impact factor: 6.005

8.  Access to a welwitindolinone core using sequential cycloadditions.

Authors:  Barry M Trost; Patrick J McDougall
Journal:  Org Lett       Date:  2009-08-20       Impact factor: 6.005

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.  Microtubule effects of welwistatin, a cyanobacterial indolinone that circumvents multiple drug resistance.

Authors:  X Zhang; C D Smith
Journal:  Mol Pharmacol       Date:  1996-02       Impact factor: 4.436
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  14 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.  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

4.  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

5.  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

6.  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

7.  Scalable Total Syntheses of (-)-Hapalindole U and (+)-Ambiguine H.

Authors:  Thomas J Maimone; Yoshihiro Ishihara; Phil S Baran
Journal:  Tetrahedron       Date:  2015-05-02       Impact factor: 2.457

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.  Studies toward welwitindolinones: formal syntheses of N-methylwelwitindolinone C isothiocyanate and related natural products.

Authors:  Tsung-Hao Fu; William T McElroy; Mariam Shamszad; Richard W Heidebrecht; Brian Gulledge; Stephen F Martin
Journal:  Tetrahedron       Date:  2013-07-08       Impact factor: 2.457
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