Literature DB >> 21142214

Synthesis of tylocrebrine and related phenanthroindolizidines by VOF3-mediated oxidative aryl-alkene coupling.

Micah J Niphakis1, Gunda I Georg.   

Abstract

A highly convergent strategy to prepare phenanthroindolizidines is reported involving three consecutive C-C coupling reactions. This sequence features a novel VOF(3)-mediated aryl-alkene coupling in the final step, which enables regioselective preparation of C5-substituted phenanthroindolizidines for the first time. This strategy has been applied to the synthesis of eight natural and unnatural members in this class to investigate the scope of this chemistry and to explore structure-activity relationships.

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Year:  2010        PMID： 21142214     DOI： 10.1021/ol1023954

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


  10 in total

1.  Enantiospecific Synthesis and Biological Investigations of a Nuphar Alkaloid: Proposed Structure of a Castoreum Component.

Authors:  Hajime Seki; Gunda I Georg
Journal:  European J Org Chem       Date:  2014-06-01

2.  Direct Hiyama cross-coupling of enaminones with triethoxy(aryl)silanes and dimethylphenylsilanol.

Authors:  Lei Bi; Gunda I Georg
Journal:  Org Lett       Date:  2011-09-22       Impact factor: 6.005

3.  Three-component synthesis of cyclic enaminones via ketene cyclization.

Authors:  Hajime Seki; Gunda I Georg
Journal:  Org Lett       Date:  2011-04-01       Impact factor: 6.005

4.  Total Syntheses and Cytotoxicity of (R)- and (S)-Boehmeriasin A.

Authors:  Matthew W Leighty; Gunda I Georg
Journal:  ACS Med Chem Lett       Date:  2011-04-14       Impact factor: 4.345

5.  Palladium-catalyzed direct C-H arylation of cyclic enaminones with aryl iodides.

Authors:  Yi-Yun Yu; Lei Bi; Gunda I Georg
Journal:  J Org Chem       Date:  2013-06-10       Impact factor: 4.354

6.  Regioselective C5-alkylation and C5-methylcarbamate formation of 2,3-dihydro-4-pyridones and C3-alkylation and C3-methylcarbamate formation of 4-(pyrrolidin-1-yl)furan-2(5H)-one.

Authors:  Xingxian Gu; Gunda I Georg
Journal:  Tetrahedron Lett       Date:  2015-10-21       Impact factor: 2.415

7.  Copper-assisted palladium(II)-catalyzed direct arylation of cyclic enaminones with arylboronic acids.

Authors:  Yong Wook Kim; Micah J Niphakis; Gunda I Georg
Journal:  J Org Chem       Date:  2012-10-22       Impact factor: 4.354

8.  Reformulating Tylocrebrine in Epidermal Growth Factor Receptor Targeted Polymeric Nanoparticles Improves Its Therapeutic Index.

Authors:  Ameya R Kirtane; Henry L Wong; Bharath Raja Guru; Lev G Lis; Gunda I Georg; Vadim J Gurvich; Jayanth Panyam
Journal:  Mol Pharm       Date:  2015-07-03       Impact factor: 4.939

9.  Boron-Heck reaction of cyclic enaminones: regioselective direct arylation via oxidative palladium(II) catalysis.

Authors:  Yong Wook Kim; Gunda I Georg
Journal:  Org Lett       Date:  2014-03-03       Impact factor: 6.005

10.  Enantioselective synthesis of 3,4-dihydro-1,2-oxazepin-5(2H)-ones and 2,3-dihydropyridin-4(1H)-ones from β-substituted β-hydroxyaminoaldehydes.

Authors:  Adwait R Ranade; Gunda I Georg
Journal:  J Org Chem       Date:  2014-01-13       Impact factor: 4.354
  10 in total

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