Literature DB >> 24123612

Enantiospecific total synthesis of N-methylwelwitindolinone D isonitrile.

Evan D Styduhar1, Alexander D Huters, Nicholas A Weires, Neil K Garg.   

Abstract

The total synthesis of N-methylwelwitindolinone D isonitrile (1) has been achieved in 17 steps from a readily available carvone derivative. The route features a double C-H functionalization event involving a keto oxindole substrate to introduce the tetrahydrofuran ring of the natural product.
Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  C-H functionalization; natural products; nitrene insertion; total synthesis; welwitindolinone

Mesh：

Substances：

Year:  2013        PMID： 24123612      PMCID： PMC3892424          DOI： 10.1002/anie.201307464

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


  38 in total

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3.  Total synthesis of (-)-N-methylwelwitindolinone C isothiocyanate.

Authors:  Alexander D Huters; Kyle W Quasdorf; Evan D Styduhar; Neil K Garg
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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.  Rapid access to the Welwitindolinone alkaloid skeleton by cyclization of indolecarboxaldehyde substituted cyclohexanones.

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8.  Indolyne experimental and computational studies: synthetic applications and origins of selectivities of nucleophilic additions.

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Journal:  J Am Chem Soc       Date:  2010-11-29       Impact factor: 15.419

9.  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
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Authors:  Adam E Goetz; Neil K Garg
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Authors:  Thomas J Maimone; Yoshihiro Ishihara; Phil S Baran
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4.  Total synthesis of (-)-N-methylwelwitindolinone B isothiocyanate via a chlorinative oxabicycle ring-opening strategy.

Authors:  Nicholas A Weires; Evan D Styduhar; Emma L Baker; Neil K Garg
Journal:  J Am Chem Soc       Date:  2014-10-10       Impact factor: 15.419

Review 5.  Recent advances in hapalindole-type cyanobacterial alkaloids: biosynthesis, synthesis, and biological activity.

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Journal:  Nat Prod Rep       Date:  2021-09-23       Impact factor: 15.111

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Authors:  Adam E Goetz; Amanda L Silberstein; Michael A Corsello; Neil K Garg
Journal:  J Am Chem Soc       Date:  2014-02-18       Impact factor: 15.419

Review 7.  Leveraging Fleeting Strained Intermediates to Access Complex Scaffolds.

Authors:  Sarah M Anthony; Laura G Wonilowicz; Matthew S McVeigh; Neil K Garg
Journal:  JACS Au       Date:  2021-06-23
  7 in total

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