Literature DB >> 21819133

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

Alexander D Huters1, Kyle W Quasdorf, Evan D Styduhar, Neil K Garg.   

Abstract

We report the first total synthesis of (-)-N-methylwelwitindolinone C isothiocyanate. Our route features a number of key transformations, including an indolyne cyclization to assemble the [4.3.1]-bicyclic scaffold, as well as a late-stage intramolecular nitrene insertion to functionalize the C11 bridgehead carbon en route to the natural product.

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Year:  2011        PMID： 21819133      PMCID： PMC3188348          DOI： 10.1021/ja206538k

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  39 in total

1.  A silver-catalyzed intramolecular amidation of saturated C--h bonds.

Authors:  Yong Cui; Chuan He
Journal:  Angew Chem Int Ed Engl       Date:  2004-08-13       Impact factor: 15.336

2.  Bridgehead enolates and bridgehead alkenes in a welwistatin model series.

Authors:  Valerie Boissel; Nigel S Simpkins; Gurdip Bhalay; Alexander J Blake; William Lewis
Journal:  Chem Commun (Camb)       Date:  2009-01-21       Impact factor: 6.222

3.  A stereoselective synthesis of (-)-tetrodotoxin.

Authors:  Andrew Hinman; J Du Bois
Journal:  J Am Chem Soc       Date:  2003-09-24       Impact factor: 15.419

4.  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

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.  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

7.  Application of 6,7-indole aryne cycloaddition and Pd(0)-catalyzed Suzuki-Miyaura and Buchwald-Hartwig cross-coupling reactions for the preparation of annulated indole libraries.

Authors:  Paul D Thornton; Neil Brown; David Hill; Ben Neuenswander; Gerald H Lushington; Conrad Santini; Keith R Buszek
Journal:  ACS Comb Sci       Date:  2011-06-30       Impact factor: 3.784

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

Authors:  G-Yoon J Im; Sarah M Bronner; Adam E Goetz; Robert S Paton; Paul H-Y Cheong; K N Houk; Neil K Garg
Journal:  J Am Chem Soc       Date:  2010-11-29       Impact factor: 15.419

9.  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

10.  Indolynes as electrophilic indole surrogates: fundamental reactivity and synthetic applications.

Authors:  Sarah M Bronner; Kevin B Bahnck; Neil K Garg
Journal:  Org Lett       Date:  2009-02-19       Impact factor: 6.005
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  23 in total

1.  Total synthesis: Welwitindolinone is well worth it.

Authors:  John L Wood
Journal:  Nat Chem       Date:  2012-04-23       Impact factor: 24.427

2.  An efficient computational model to predict the synthetic utility of heterocyclic arynes.

Authors:  Adam E Goetz; Sarah M Bronner; Jordan D Cisneros; Joshua M Melamed; Robert S Paton; K N Houk; Neil K Garg
Journal:  Angew Chem Int Ed Engl       Date:  2012-02-03       Impact factor: 15.336

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.  Computational predictions of substituted benzyne and indolyne regioselectivities.

Authors:  Elias Picazo; K N Houk; Neil K Garg
Journal:  Tetrahedron Lett       Date:  2015-06-03       Impact factor: 2.415

5.  Identification and characterization of a welwitindolinone alkaloid biosynthetic gene cluster in the stigonematalean Cyanobacterium Hapalosiphon welwitschii.

Authors:  Matthew L Hillwig; Heather A Fuhrman; Kuljira Ittiamornkul; Tyler J Sevco; Daniel H Kwak; Xinyu Liu
Journal:  Chembiochem       Date:  2014-03-21       Impact factor: 3.164

6.  Expanding the Strained Alkyne Toolbox: Generation and Utility of Oxygen-Containing Strained Alkynes.

Authors:  Tejas K Shah; Jose M Medina; Neil K Garg
Journal:  J Am Chem Soc       Date:  2016-03-29       Impact factor: 15.419

7.  Nickel-Catalyzed Conversion of Enol Triflates into Alkenyl Halides.

Authors:  Julie L Hofstra; Kelsey E Poremba; Alex M Shimozono; Sarah E Reisman
Journal:  Angew Chem Int Ed Engl       Date:  2019-09-19       Impact factor: 15.336

8.  New Hindered Amide Base for Aryne Insertion into Si-P, Si-S, Si-N, and C-C Bonds.

Authors:  Milad Mesgar; Justin Nguyen-Le; Olafs Daugulis
Journal:  J Am Chem Soc       Date:  2018-10-10       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.  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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