Literature DB >> 20161552

Total Syntheses of Naamidine G and 14-Methoxynaamidine G.

Panduka B Koswatta1, Carl J Lovely.   

Abstract

Simple total syntheses of two Leucetta-derived marine alkaloids have been developed using position specific halogen-metal exchange of polyhaloimidazoles to introduce the benzyl substituted sidechains. Introduction of the C2 amine group by lithiation and trapping with tosyl azide provides amines on catalytic hydrogenation, which can be converted to naamidine G and 14-methoxynaamidine G using a procedure described in the literature.

Entities:  

Year:  2010        PMID: 20161552      PMCID: PMC2805157          DOI: 10.1016/j.tetlet.2009.10.117

Source DB:  PubMed          Journal:  Tetrahedron Lett        ISSN: 0040-4039            Impact factor:   2.415


  14 in total

1.  A concise total synthesis of naamidine A.

Authors:  Nicholas S Aberle; Guillaume Lessene; Keith G Watson
Journal:  Org Lett       Date:  2006-02-02       Impact factor: 6.005

2.  Synthesis of marine alkaloids from the oroidin family.

Authors:  Hans-Dieter Arndt; Matthias Riedrich
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

3.  Preparation of new polyfunctional magnesiated heterocycles using a chlorine-, bromine-, or iodine-magnesium exchange

Authors: 
Journal:  J Org Chem       Date:  2000-07-28       Impact factor: 4.354

4.  A new structural theme in the imidazole-containing alkaloids from a calcareous Leucetta sponge.

Authors:  Paul Ralifo; Phillip Crews
Journal:  J Org Chem       Date:  2004-12-24       Impact factor: 4.354

5.  Selective functionalization of imidazoles via an iodine-copper exchange reaction.

Authors:  Xiaoyin Yang; Paul Knochel
Journal:  Chem Commun (Camb)       Date:  2006-04-20       Impact factor: 6.222

6.  Total synthesis of (+/-)-calcaridine A and (+/-)-epi-calcaridine A.

Authors:  Panduka B Koswatta; Rasapalli Sivappa; H V Rasika Dias; Carl J Lovely
Journal:  Org Lett       Date:  2008-09-25       Impact factor: 6.005

7.  Total synthesis of the putative structure of nagelamide D.

Authors:  Manojkumar R Bhandari; Rasapalli Sivappa; Carl J Lovely
Journal:  Org Lett       Date:  2009-04-02       Impact factor: 6.005

8.  Structure revision of spiroleucettadine, a sponge alkaloid with a bicyclic core meager in H-atoms.

Authors:  Kimberly N White; Taro Amagata; Allen G Oliver; Karen Tenney; Philip J Wenzel; Phillip Crews
Journal:  J Org Chem       Date:  2008-10-17       Impact factor: 4.354

9.  Addition-hydroamination reactions of propargyl cyanamides: rapid access to highly substituted 2-aminoimidazoles.

Authors:  Robert L Giles; John D Sullivan; Andrew M Steiner; Ryan E Looper
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

10.  Preparation and Diels-Alder chemistry of 4-vinylimidazoles.

Authors:  Carl J Lovely; Hongwang Du; Rasapalli Sivappa; Manojkumar R Bhandari; Yong He; H V Rasika Dias
Journal:  J Org Chem       Date:  2007-04-11       Impact factor: 4.354

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  6 in total

1.  Total syntheses of isonaamine C and isonaamidine E.

Authors:  Heather M Lima; Beatriz J Garcia-Barboza; Nicole N Khatibi; Carl J Lovely
Journal:  Tetrahedron Lett       Date:  2011-11-02       Impact factor: 2.415

2.  Total synthesis of 7'-desmethylkealiiquinone.

Authors:  Heather M Lima; Rasapalli Sivappa; Muhammed Yousufuddin; Carl J Lovely
Journal:  Org Lett       Date:  2012-04-24       Impact factor: 6.005

3.  Total synthesis and cytotoxicity of Leucetta alkaloids.

Authors:  Panduka B Koswatta; Sabha Kasiri; Jayanta K Das; Arunoday Bhan; Heather M Lima; Beatriz Garcia-Barboza; Nicole N Khatibi; Muhammed Yousufuddin; Subhrangsu S Mandal; Carl J Lovely
Journal:  Bioorg Med Chem       Date:  2017-01-20       Impact factor: 3.641

4.  Synthesis of 2-imidazolones and 2-iminoimidazoles.

Authors:  Heather M Lima; Carl J Lovely
Journal:  Org Lett       Date:  2011-10-12       Impact factor: 6.005

5.  Total syntheses of kealiinines A-C.

Authors:  Jayanta Das; Panduka B Koswatta; J Daniel Jones; Muhammed Yousufuddin; Carl J Lovely
Journal:  Org Lett       Date:  2012-12-05       Impact factor: 6.005

6.  Naamines and Naamidines as Novel Agents against a Plant Virus and Phytopathogenic Fungi.

Authors:  Pengbin Guo; Gang Li; Yuxiu Liu; Aidang Lu; Ziwen Wang; Qingmin Wang
Journal:  Mar Drugs       Date:  2018-09-03       Impact factor: 5.118

  6 in total

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