Literature DB >> 22962500

Lessons Learned while Traversing the Welwitindolinone Alkaloids Obstacle Course.

Vikram Bhat1, James A Mackay, Viresh H Rawal.   

Abstract

We recount several unexpected results observed in the course of our work toward the synthesis of welwitindolinone alkaloids. The surprising results provide an opportunity to refine one's understanding of the interplay between chemical structure and reactivity.

Entities:  

Year:  2011        PMID： 22962500      PMCID： PMC3434954          DOI： 10.1016/j.tet.2011.09.088

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


  29 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.  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

3.  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

4.  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

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.  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

7.  Palladium-catalyzed conversion of aryl and vinyl triflates to bromides and chlorides.

Authors:  Xiaoqiang Shen; Alan M Hyde; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2010-10-13       Impact factor: 15.419

8.  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

9.  A mild synthesis of vinyl halides and gem-dihalides using triphenyl phosphite-halogen-based reagents.

Authors:  Alberto Spaggiari; Daniele Vaccari; Paolo Davoli; Giovanni Torre; Fabio Prati
Journal:  J Org Chem       Date:  2007-02-13       Impact factor: 4.354

10.  First catalytic and green synthesis of aryl-(Z)-vinyl chlorides and its plausible addition-elimination mechanism.

Authors:  Weike Su; Can Jin
Journal:  Org Lett       Date:  2007-02-23       Impact factor: 6.005
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  6 in total

1.  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

2.  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

3.  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

4.  Reductive Chlorination and Bromination of Ketones via Trityl Hydrazones.

Authors:  Julius R Reyes; Viresh H Rawal
Journal:  Angew Chem Int Ed Engl       Date:  2016-01-28       Impact factor: 16.823

Review 5.  Recent advances in hapalindole-type cyanobacterial alkaloids: biosynthesis, synthesis, and biological activity.

Authors:  Robert M Hohlman; David H Sherman
Journal:  Nat Prod Rep       Date:  2021-09-23       Impact factor: 15.111

6.  Total Synthesis of the Chlorinated Pentacyclic Indole Alkaloid (+)-Ambiguine G.

Authors:  Lingbowei Hu; Viresh H Rawal
Journal:  J Am Chem Soc       Date:  2021-07-19       Impact factor: 15.419
  6 in total

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