Literature DB >> 20222695

Dictazoles: potential vinyl cyclobutane biosynthetic precursors to the dictazolines.

Jingqiu Dai1, Jorge I Jiménez, Michelle Kelly, Philip G Williams.   

Abstract

We report here the isolation of five new compounds, class="Chemical">dictazoles A and B (1 and 2) and <class="Chemical">span class="Chemical">dictazolines C-E (5-7). Evidence is presented for the direct conversion of the cyclobutyl analogue 1 to its cyclohexyl constitutional isomer 5 via a vinyl cyclobutane rearrangement.

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Year:  2010        PMID: 20222695      PMCID: PMC2849972          DOI: 10.1021/jo902566n

Source DB:  PubMed          Journal:  J Org Chem        ISSN: 0022-3263            Impact factor:   4.354


  10 in total

Review 1.  Marine natural products.

Authors:  John W Blunt; Brent R Copp; Wan-Ping Hu; Murray H G Munro; Peter T Northcote; Michèle R Prinsep
Journal:  Nat Prod Rep       Date:  2008-01-03       Impact factor: 13.423

2.  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

3.  Total synthesis of dimeric pyrrole-imidazole alkaloids: sceptrin, ageliferin, nagelamide e, oxysceptrin, nakamuric acid, and the axinellamine carbon skeleton.

Authors:  Daniel P O'Malley; Ke Li; Michael Maue; Alexandros L Zografos; Phil S Baran
Journal:  J Am Chem Soc       Date:  2007-03-22       Impact factor: 15.419

4.  1H and 13C NMR spectra and solution structures of novel derivatives of 5-substituted creatinines.

Authors:  Hanna Krawczyk; Agnieszka Pietras; Anna Kraska
Journal:  Spectrochim Acta A Mol Biomol Spectrosc       Date:  2006-08-21       Impact factor: 4.098

5.  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

6.  Nagelamides A-H, new dimeric bromopyrrole alkaloids from marine sponge Agelas species.

Authors:  Tadashi Endo; Masashi Tsuda; Tadashi Okada; Shinya Mitsuhashi; Hiroshi Shima; Kunimi Kikuchi; Yuzuru Mikami; Jane Fromont; Jun'ichi Kobayashi
Journal:  J Nat Prod       Date:  2004-08       Impact factor: 4.050

7.  Molecular rearrangements through thermal [1,3] carbon shifts.

Authors:  John E Baldwin; Phyllis A Leber
Journal:  Org Biomol Chem       Date:  2007-10-11       Impact factor: 3.876

8.  Dictazolines A and B, bisspiroimidazolidinones from the marine sponge Smenospongia cerebriformis.

Authors:  Jingqiu Dai; Jorge I Jiménez; Michelle Kelly; Shawn Barnes; Patricia Lorenzo; Philip Williams
Journal:  J Nat Prod       Date:  2008-06-12       Impact factor: 4.050

Review 9.  Progress toward a practical BACE-1 inhibitor.

Authors:  Ivory D Hills; Joseph P Vacca
Journal:  Curr Opin Drug Discov Devel       Date:  2007-07

Review 10.  Has the amyloid cascade hypothesis for Alzheimer's disease been proved?

Authors:  John Hardy
Journal:  Curr Alzheimer Res       Date:  2006-02       Impact factor: 3.498

  10 in total
  8 in total

Review 1.  Natural products as a source of Alzheimer's drug leads.

Authors:  Philip Williams; Analia Sorribas; Melanie-Jayne R Howes
Journal:  Nat Prod Rep       Date:  2010-11-12       Impact factor: 13.423

2.  Total synthesis and structural revision of the piperarborenines via sequential cyclobutane C-H arylation.

Authors:  Will R Gutekunst; Phil S Baran
Journal:  J Am Chem Soc       Date:  2011-11-08       Impact factor: 15.419

3.  Recent Advances in the Synthesis of Cyclobutanes by Olefin [2 + 2] Photocycloaddition Reactions.

Authors:  Saner Poplata; Andreas Tröster; You-Quan Zou; Thorsten Bach
Journal:  Chem Rev       Date:  2016-03-28       Impact factor: 60.622

4.  Araiosamines A-D: tris-bromoindole cyclic guanidine alkaloids from the marine sponge Clathria (Thalysias) araiosa.

Authors:  Xiaomei Wei; Niel M Henriksen; Jack J Skalicky; Mary Kay Harper; Thomas E Cheatham; Chris M Ireland; Ryan M Van Wagoner
Journal:  J Org Chem       Date:  2011-04-11       Impact factor: 4.354

5.  Bioactive marine drugs and marine biomaterials for brain diseases.

Authors:  Clara Grosso; Patrícia Valentão; Federico Ferreres; Paula B Andrade
Journal:  Mar Drugs       Date:  2014-05-02       Impact factor: 5.118

Review 6.  Marine Indole Alkaloids.

Authors:  Natalie Netz; Till Opatz
Journal:  Mar Drugs       Date:  2015-08-06       Impact factor: 5.118

7.  Applications of C-H functionalization logic to cyclobutane synthesis.

Authors:  Will R Gutekunst; Phil S Baran
Journal:  J Org Chem       Date:  2014-02-27       Impact factor: 4.354

8.  Enantioselective gold-catalyzed intermolecular [2+2] versus [4+2]-cycloadditions of 3-styrylindoles with N-allenamides: observation of interesting substituent effects.

Authors:  Yidong Wang; Peichao Zhang; Yuan Liu; Fei Xia; Junliang Zhang
Journal:  Chem Sci       Date:  2015-06-23       Impact factor: 9.825

  8 in total

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