Literature DB >> 22783971

Synthesis of functionalized cyclohexenone core of welwitindolinones via rhodium-catalyzed [5 + 1] cycloaddition.

Min Zhang1, Weiping Tang.   

Abstract

The cyclohexenone core of welwitindolinones was synthesized by a Rh(I)-catalyzed [5 + 1]-cycloaddition of an allenylcyclopropane with CO. A pentasubstituted cyclopropane was prepared successfully by a Rh(II)-catalyzed intramolecular cyclopropanation of alkenes with chlorodiazoacetates.

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Year:  2012        PMID： 22783971      PMCID： PMC3480994          DOI： 10.1021/ol301614v

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


  43 in total

1.  Iridium-Catalyzed [5 + 1] Cycloaddition: Allenylcyclopropane as a Five-Carbon Assembling Unit.

Authors:  Masahiro Murakami; Kenichiro Itami; Minoru Ubukata; Itaru Tsuji; Yoshihiko Ito
Journal:  J Org Chem       Date:  1998-01-09       Impact factor: 4.354

2.  Transition metal chemistry of cyclopropenes and cyclopropanes.

Authors:  Michael Rubin; Marina Rubina; Vladimir Gevorgyan
Journal:  Chem Rev       Date:  2007-07       Impact factor: 60.622

3.  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

4.  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

5.  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

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.  Synthesis of highly functionalized cyclohexenone rings: rhodium-catalyzed 1,3-acyloxy migration and subsequent [5+1] cycloaddition.

Authors:  Dongxu Shu; Xiaoxun Li; Min Zhang; Patrick J Robichaux; Weiping Tang
Journal:  Angew Chem Int Ed Engl       Date:  2010-12-29       Impact factor: 15.336

9.  How easy are the syntheses of allenes?

Authors:  Shichao Yu; Shengming Ma
Journal:  Chem Commun (Camb)       Date:  2011-03-15       Impact factor: 6.222

10.  Rh(I)-catalyzed [5+1] cycloaddition of vinylcyclopropanes and CO for the synthesis of α,β- and β,γ-cyclohexenones.

Authors:  Guo-Jie Jiang; Xu-Fei Fu; Qian Li; Zhi-Xiang Yu
Journal:  Org Lett       Date:  2012-01-18       Impact factor: 6.005
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  5 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.  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

3.  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

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

5.  Transition Metal-Catalyzed Selective Carbon-Carbon Bond Cleavage of Vinylcyclopropanes in Cycloaddition Reactions.

Authors:  Jianhua Wang; Stephanie A Blaszczyk; Xiaoxun Li; Weiping Tang
Journal:  Chem Rev       Date:  2020-08-05       Impact factor: 72.087
  5 in total

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