Literature DB >> 17078699

A synthesis of the welwistatin core.

Ryan Lauchli1, Kenneth J Shea.   

Abstract

[Structure: see text] An approach to the core structure of the microtubule-targeting agent welwistatin is described. The approach utilizes the type 2 intramolecular Diels-Alder reaction, with indole serving as the tether between diene and dienophile, to form the natural product's characteristic bicyclo[4.3.1]decane skeleton.

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Year:  2006        PMID： 17078699     DOI： 10.1021/ol0620747

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


  18 in total

1.  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

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.  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.  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

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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