Literature DB >> 22830424

Formal syntheses of naturally occurring welwitindolinones.

Tsung-hao Fu1, William T McElroy, Mariam Shamszad, Stephen F Martin.   

Abstract

The formal syntheses of N-methylwelwitindolinone C isothiocyanate, N-methylwelwitindolinone C isonitrile, N-methylwelwitindolinone D isonitrile, 3-hydroxy-N-methylwelwitindolinone C isothiocyanate, and 3-hydroxy-N-methylwelwitindolinone C isonitrile are reported. The synthesis features several novel processes, including a Lewis acid mediated coupling between a benzylic-type heteroaromatic alcohol and a highly functionalized silyl ketene acetal, an intramolecular enolate arylation, and a regioselective, Pd(0)-catalyzed π-allylic cyclization of a γ-benzoyloxy enone moiety that is revealed by unmasking a furan ring.

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Year:  2012        PMID： 22830424      PMCID： PMC3416027          DOI： 10.1021/ol301424h

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


  36 in total

1.  STUDIES ON STEROIDAL COMPOUNDS. X. PREPARATION OF 17BETA-CHLORO STEROIDS.

Authors:  H MORI; K TSUNEDA
Journal:  Chem Pharm Bull (Tokyo)       Date:  1963-11       Impact factor: 1.645

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.  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.  Stereocontrolled synthesis of 20,21-dihydro N-methylwelwitindolinone B isothiocyanate.

Authors:  Vikram Bhat; Viresh H Rawal
Journal:  Chem Commun (Camb)       Date:  2011-07-27       Impact factor: 6.222

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.  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.

Authors:  Jérôme Baudoux; Alexander J Blake; Nigel S Simpkins
Journal:  Org Lett       Date:  2005-09-15       Impact factor: 6.005

8.  A mild synthesis of vinyl halides and gem-dihalides using triphenyl phosphite-halogen-based reagents.

Authors:  Alberto Spaggiari; Daniele Vaccari; Paolo Davoli; Giovanni Torre; Fabio Prati
Journal:  J Org Chem       Date:  2007-02-13       Impact factor: 4.354

9.  Synthesis of β-Heteroaryl Propionates via Trapping of Carbocations with π-Nucleophiles.

Authors:  Tsung-Hao Fu; Amy Bonaparte; Stephen F Martin
Journal:  Tetrahedron Lett       Date:  2009-07-01       Impact factor: 2.415

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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  7 in total

1.  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

2.  Natural Products and Their Mimics as Targets of Opportunity for Discovery.

Authors:  Stephen F Martin
Journal:  J Org Chem       Date:  2017-09-15       Impact factor: 4.354

3.  Enantioselective total synthesis of (-)-citrinadin A and revision of its stereochemical structure.

Authors:  Zhiguo Bian; Christopher C Marvin; Stephen F Martin
Journal:  J Am Chem Soc       Date:  2013-07-18       Impact factor: 15.419

4.  Scalable Total Syntheses of (-)-Hapalindole U and (+)-Ambiguine H.

Authors:  Thomas J Maimone; Yoshihiro Ishihara; Phil S Baran
Journal:  Tetrahedron       Date:  2015-05-02       Impact factor: 2.457

5.  Concise total synthesis of (±)-actinophyllic acid.

Authors:  Brett A Granger; Ivan T Jewett; Jeffrey D Butler; Stephen F Martin
Journal:  Tetrahedron       Date:  2014-07-08       Impact factor: 2.457

6.  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

7.  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
  7 in total

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