Literature DB >> 16048307

Rapid synthesis of the N-methylwelwitindolinone skeleton.

James A MacKay1, Raynauld L Bishop, Viresh H Rawal.   

Abstract

An efficient, convergent synthesis of the core bicyclo[4.3.1]decane ring system of welwitindolinones is described. Key steps in the synthesis include an intramolecular palladium-catalyzed enolate arylation reaction to create the desired bicyclic skeleton and a Curtius rearrangement to install the bridgehead isocyanate unit. [reaction: see text]

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Year:  2005        PMID： 16048307     DOI： 10.1021/ol051043t

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


  27 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.  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.  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

6.  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

7.  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

8.  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

9.  Rotational isomers of N-methyl-N-arylacetamides and their derived enolates: implications for asymmetric Hartwig oxindole cyclizations.

Authors:  Jérémie Mandel; Xiaohong Pan; E Ben Hay; Steven J Geib; Craig S Wilcox; Dennis P Curran
Journal:  J Org Chem       Date:  2013-04-09       Impact factor: 4.354

10.  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
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