Literature DB >> 16737334

An approach to the total synthesis of welwistatin.

Thomas J Greshock1, Raymond L Funk.   

Abstract

An approach to the total synthesis of the antimicrotubule agent welwistatin is described. Key transformations include (1) a 7-endo intramolecular conjugate addition reaction of enone 6 to deliver the strained bicyclo[4.3.1]decanone 5; (2) a 6pi electrocyclic ring closure of trienecarbamate 16 followed by oxidation to afford protected aniline 17; and (3) an intramolecular cyclization of acetic acid derivative 18 to give rise to indole 19. [reaction: see text]

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Year:  2006        PMID： 16737334      PMCID： PMC2547338          DOI： 10.1021/ol0608799

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


  12 in total

1.  A mild and efficient synthesis of oxindoles: progress towards the synthesis of welwitindolinone A isonitrile.

Authors:  Joseph M Ready; Sarah E Reisman; Makoto Hirata; Matthew M Weiss; Kazuhiko Tamaki; Timo V Ovaska; John L Wood
Journal:  Angew Chem Int Ed Engl       Date:  2004-02-27       Impact factor: 15.336

2.  Rapid synthesis of the N-methylwelwitindolinone skeleton.

Authors:  James A MacKay; Raynauld L Bishop; Viresh H Rawal
Journal:  Org Lett       Date:  2005-08-04       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.  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.  Enantioselective synthesis of stephacidin B.

Authors:  Seth B Herzon; Andrew G Myers
Journal:  J Am Chem Soc       Date:  2005-04-20       Impact factor: 15.419

6.  Synthesis of indoles via 6pi-electrocyclic ring closures of trienecarbamates.

Authors:  Thomas J Greshock; Raymond L Funk
Journal:  J Am Chem Soc       Date:  2006-04-19       Impact factor: 15.419

7.  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

8.  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

9.  Welwitindolinone analogues that reverse P-glycoprotein-mediated multiple drug resistance.

Authors:  C D Smith; J T Zilfou; K Stratmann; G M Patterson; R E Moore
Journal:  Mol Pharmacol       Date:  1995-02       Impact factor: 4.436

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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  25 in total

1.  A strategy for the total synthesis of dragmacidin E. Construction of the core ring system.

Authors:  Raymond J Huntley; Raymond L Funk
Journal:  Org Lett       Date:  2006-10-12       Impact factor: 6.005

2.  Enantiospecific total synthesis of the hapalindoles, fischerindoles, and welwitindolinones via a redox economic approach.

Authors:  Jeremy M Richter; Yoshihiro Ishihara; Takeshi Masuda; Brandon W Whitefield; Tomás Llamas; Antti Pohjakallio; Phil S Baran
Journal:  J Am Chem Soc       Date:  2008-12-31       Impact factor: 15.419

3.  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

4.  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

5.  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

6.  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

7.  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

8.  A Concise Total Synthesis of Dictyodendrins F, H, and I Using Aryl Ynol Ethers as Key Building Blocks.

Authors:  Wenhan Zhang; Joseph M Ready
Journal:  J Am Chem Soc       Date:  2016-08-11       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.  Synthesis of the bicyclic welwitindolinone core via an alkylation/cyclization cascade reaction.

Authors:  John A Brailsford; Ryan Lauchli; Kenneth J Shea
Journal:  Org Lett       Date:  2009-11-19       Impact factor: 6.005
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