Literature DB >> 19278243

Total synthesis of the putative structure of nagelamide D.

Manojkumar R Bhandari1, Rasapalli Sivappa, Carl J Lovely.   

Abstract

A total synthesis of the putative structure of nagelamide D from imidazole is described. A Stille cross-coupling is used to construct the bis imidazole skeleton, and the pyrrolecarboxamides are introduced via a double Mitsunobu reaction using a pyrrolehydantoin derivative. Discrepancies between the published spectroscopic data and that reported in the literature cast doubts either on the assigned structure or the reported data.

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Year:  2009        PMID: 19278243      PMCID: PMC2668712          DOI: 10.1021/ol9001762

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


  23 in total

1.  Significant enhancement of the Stille reaction with a new combination of reagents-copper(I) iodide with cesium fluoride.

Authors:  Simon P H Mee; Victor Lee; Jack E Baldwin
Journal:  Chemistry       Date:  2005-05-20       Impact factor: 5.236

2.  Total synthesis of (+/-)-axinellamines A and B.

Authors:  Daniel P O'Malley; Junichiro Yamaguchi; Ian S Young; Ian B Seiple; Phil S Baran
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

3.  Sceptrin as a potential biosynthetic precursor to complex pyrrole-imidazole alkaloids: the total synthesis of ageliferin.

Authors:  Phil S Baran; Daniel P O'Malley; Alexandros L Zografos
Journal:  Angew Chem Int Ed Engl       Date:  2004-05-10       Impact factor: 15.336

4.  Facile synthesis of the trans-fused azabicyclo[3.3.0]octane core of the palau'amines and the tricyclic core of the axinellamines from a common intermediate.

Authors:  Manuel A Zancanella; Daniel Romo
Journal:  Org Lett       Date:  2008-08-12       Impact factor: 6.005

5.  Stylissadines A and B: the first tetrameric pyrrole-imidazole alkaloids.

Authors:  Achim Grube; Matthias Köck
Journal:  Org Lett       Date:  2006-10-12       Impact factor: 6.005

6.  Mechanism of the vinylcyclobutane rearrangement of sceptrin to ageliferin and nagelamide E.

Authors:  Brian H Northrop; Daniel P O'Malley; Alexandros L Zografos; Phil S Baran; K N Houk
Journal:  Angew Chem Int Ed Engl       Date:  2006-06-19       Impact factor: 15.336

7.  Unusually Large (13)C NMR Chemical Shift Differences between Neutral and Protonated Glycocyamidines. New Insights on Previously Reported Chemical Shift Assignments and Chemical Properties.

Authors:  Anne Olofson; Kenichi Yakushijin; David A. Horne
Journal:  J Org Chem       Date:  1998-08-21       Impact factor: 4.354

8.  Nagelamides K and L, dimeric bromopyrrole alkaloids from sponge Agelas species.

Authors:  Atsushi Araki; Takaaki Kubota; Masashi Tsuda; Yuzuru Mikami; Jane Fromont; Jun'ichi Kobayashi
Journal:  Org Lett       Date:  2008-05-03       Impact factor: 6.005

9.  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

10.  Nagelamide J, a novel dimeric bromopyrrole alkaloid from a sponge Agelas species.

Authors:  Atsushi Araki; Masashi Tsuda; Takaaki Kubota; Yuzuru Mikami; Jane Fromont; Jun'ichi Kobayashi
Journal:  Org Lett       Date:  2007-05-16       Impact factor: 6.005

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  12 in total

1.  Asymmetric total synthesis of ent-cyclooroidin.

Authors:  Sabuj Mukherjee; Rasapalli Sivappa; Muhammed Yousufuddin; Carl J Lovely
Journal:  Org Lett       Date:  2010-11-05       Impact factor: 6.005

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.  Pyrrole aminoimidazole alkaloid metabiosynthesis with marine sponges Agelas conifera and Stylissa caribica.

Authors:  E Paige Stout; Yong-Gang Wang; Daniel Romo; Tadeusz F Molinski
Journal:  Angew Chem Int Ed Engl       Date:  2012-04-04       Impact factor: 15.336

4.  Thio acid-mediated conversion of azides to amides - exploratory studies en route to oroidin alkaloids.

Authors:  Apsara K Herath; Manoj R Bhandari; Delphine Gout; Muhammed Yousufuddin; Carl J Lovely
Journal:  Tetrahedron Lett       Date:  2017-08-24       Impact factor: 2.415

5.  Preparation and Diels-Alder reactions of 1'-heterosubsituted vinylimidazoles.

Authors:  Abhisek Ray; Sabuj Mukherjee; Jayanta Das; Manoj K Bhandari; Hongwang Du; Muhammed Yousufuddin; Carl J Lovely
Journal:  Tetrahedron Lett       Date:  2015-06-03       Impact factor: 2.415

6.  Diversity-oriented approach to pyrrole-imidazole alkaloid frameworks.

Authors:  Manojkumar R Bhandari; Muhammed Yousufuddin; Carl J Lovely
Journal:  Org Lett       Date:  2011-02-21       Impact factor: 6.005

7.  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

8.  Total Syntheses of Naamidine G and 14-Methoxynaamidine G.

Authors:  Panduka B Koswatta; Carl J Lovely
Journal:  Tetrahedron Lett       Date:  2010-01-06       Impact factor: 2.415

9.  Synthesis of 7-(15)N-Oroidin and evaluation of utility for biosynthetic studies of pyrrole-imidazole alkaloids by microscale (1)H-(15)N HSQC and FTMS.

Authors:  Yong-Gang Wang; Brandon I Morinaka; Jeremy Chris P Reyes; Jeremy J Wolff; Daniel Romo; Tadeusz F Molinski
Journal:  J Nat Prod       Date:  2010-03-26       Impact factor: 4.050

Review 10.  A submarine journey: the pyrrole-imidazole alkaloids.

Authors:  Barbara Forte; Beatrice Malgesini; Claudia Piutti; Francesca Quartieri; Alessandra Scolaro; Gianluca Papeo
Journal:  Mar Drugs       Date:  2009-11-27       Impact factor: 5.118

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