Literature DB >> 19860385

Synthesis of the bicyclic welwitindolinone core via an alkylation/cyclization cascade reaction.

John A Brailsford1, Ryan Lauchli, Kenneth J Shea.   

Abstract

Synthesis of an advanced welwitindolinone intermediate via an alkylation/cyclization reaction is reported. The key step involves a one pot Lewis acid-mediated alkylation of a silylketene aminal with a furan alcohol followed by an intramolecular cyclization. The reaction is stereoselective and takes place at low temperature. The cycloadduct was highly functionalized and contains the welwitindolinone core structure.

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Year:  2009        PMID： 19860385      PMCID： PMC2784123          DOI： 10.1021/ol902173g

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


  20 in total

1.  Studies toward diazonamide A: initial synthetic forays directed toward the originally proposed structure.

Authors:  K C Nicolaou; Scott A Snyder; Xianhai Huang; Klaus B Simonsen; Alexandros E Koumbis; Antony Bigot
Journal:  J Am Chem Soc       Date:  2004-08-18       Impact factor: 15.419

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.  Total synthesis of marine natural products without using protecting groups.

Authors:  Phil S Baran; Thomas J Maimone; Jeremy M Richter
Journal:  Nature       Date:  2007-03-22       Impact factor: 49.962

4.  Aryllead(IV) reagents in synthesis: formation of the C11 quaternary center of N-methylwelwitindolinone C isothiocyanate.

Authors:  H Deng; J P Konopelski
Journal:  Org Lett       Date:  2001-09-20       Impact factor: 6.005

5.  A synthesis of the welwistatin core.

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

6.  A versatile synthesis of unsymmetrical 3,3'-bioxindoles: stereoselective Mukaiyama aldol reactions of 2-siloxyindoles with isatins.

Authors:  J Michael Ellis; Larry E Overman; Huw R Tanner; Jocelyn Wang
Journal:  J Org Chem       Date:  2008-10-15       Impact factor: 4.354

7.  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

8.  Structure of P-glycoprotein reveals a molecular basis for poly-specific drug binding.

Authors:  Stephen G Aller; Jodie Yu; Andrew Ward; Yue Weng; Srinivas Chittaboina; Rupeng Zhuo; Patina M Harrell; Yenphuong T Trinh; Qinghai Zhang; Ina L Urbatsch; Geoffrey Chang
Journal:  Science       Date:  2009-03-27       Impact factor: 47.728

9.  Concise synthesis of the bicyclic scaffold of N-methylwelwitindolinone C isothiocyanate via an indolyne cyclization.

Authors:  Xia Tian; Alexander D Huters; Colin J Douglas; Neil K Garg
Journal:  Org Lett       Date:  2009-06-04       Impact factor: 6.005

10.  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
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  16 in total

1.  Synthetic Studies on the Ambiguine Family of Alkaloids: Construction of the ABCD Ring System.

Authors:  Ryan J Rafferty; Robert M Williams
Journal:  Tetrahedron Lett       Date:  2011-04-27       Impact factor: 2.415

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

Authors:  Richard W Heidebrecht; Brian Gulledge; Stephen F Martin
Journal:  Org Lett       Date:  2010-06-04       Impact factor: 6.005

5.  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

6.  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

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

Authors:  David B Freeman; 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
Journal:  Tetrahedron       Date:  2010-08-14       Impact factor: 2.457

8.  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

9.  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

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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