Literature DB >> 17685656

Welwistatin support studies: expansion and limitation of aryllead(IV) coupling reactions.

Jibo Xia1, Lauren E Brown, Joseph P Konopelski.   

Abstract

Recent support studies on the total synthesis of the welwistatin system are described. The target step involves lead-mediated arylation of sterically demanding aryl groups and carbon acid coupling partners in order to establish the highly congested tetracyclic core structure. Type 7 beta-ketoesters and beta-ketonitriles were successfully arylated with a variety of ortho- and meta-substituted aryllead compounds generated by a halogen-boron-lead exchange sequence. The enolates of compounds 15, 19, and 25, each bearing all-carbon quaternary centers adjacent to the arylation site, failed to couple.

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Year:  2007        PMID： 17685656      PMCID： PMC2525610          DOI： 10.1021/jo071156l

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  18 in total

1.  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

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.  Total synthesis of (+/-)-jiadifenin, a non-peptidyl neurotrophic modulator.

Authors:  Young Shin Cho; David A Carcache; Yuan Tian; Yue-Ming Li; Samuel J Danishefsky
Journal:  J Am Chem Soc       Date:  2004-11-10       Impact factor: 15.419

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.  Catalytic asymmetric synthesis of all-carbon quaternary stereocenters.

Authors:  Christopher J Douglas; Larry E Overman
Journal:  Proc Natl Acad Sci U S A       Date:  2004-01-14       Impact factor: 11.205

Review 9.  Contiguous stereogenic quaternary carbons: a daunting challenge in natural products synthesis.

Authors:  Emily A Peterson; Larry E Overman
Journal:  Proc Natl Acad Sci U S A       Date:  2004-07-01       Impact factor: 11.205

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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  15 in total

1.  Total syntheses and structural revision of alpha- and beta-diversonolic esters and total syntheses of diversonol and blennolide C.

Authors:  K C Nicolaou; Ang Li
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

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.  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

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.  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

7.  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

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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