Literature DB >> 20715768

Room-temperature aromatization of tetrahydro-β-carbolines by 2-iodoxybenzoic acid: utility in a total synthesis of eudistomin U.

Joseph D Panarese1, Stephen P Waters.   

Abstract

2-Iodoxybenzoic acid is a convenient reagent for the dehydrogenation of tetrahydro-β-carbolines to their aromatic forms under mild conditions. The utility of the method was demonstrated in a total synthesis of the marine indole alkaloid eudistomin U.

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Year:  2010        PMID: 20715768      PMCID: PMC2937063          DOI: 10.1021/ol101688x

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


  26 in total

1.  Synthesis and biological evaluation of novel beta-carboline derivatives as Tat-TAR interaction inhibitors.

Authors:  Xiaolin Yu; Wei Lin; Jingyun Li; Ming Yang
Journal:  Bioorg Med Chem Lett       Date:  2004-06-21       Impact factor: 2.823

2.  o-Iodoxybenzoic acid- and tetraethylammonium bromide-mediated oxidative transformation of primary carboxamides to one-carbon dehomologated nitriles.

Authors:  Dinesh S Bhalerao; Ulhas S Mahajan; Kiran H Chaudhari; Krishnacharya G Akamanchi
Journal:  J Org Chem       Date:  2007-01-19       Impact factor: 4.354

3.  New reactions of IBX: oxidation of nitrogen- and sulfur-containing substrates to afford useful synthetic intermediates.

Authors:  K C Nicolaou; Casey J N Mathison; Tamsyn Montagnon
Journal:  Angew Chem Int Ed Engl       Date:  2003-09-05       Impact factor: 15.336

4.  Antimalarial activity of a new family of analogues of manzamine A.

Authors:  Jeffrey D Winkler; Allyn T Londregan; Mark T Hamann
Journal:  Org Lett       Date:  2006-06-08       Impact factor: 6.005

5.  Synthesis of 6-substituted beta-carbolines that behave as benzodiazepine receptor antagonists or inverse agonists.

Authors:  T J Hagen; P Skolnick; J M Cook
Journal:  J Med Chem       Date:  1987-04       Impact factor: 7.446

6.  Synthesis and biological studies of 1-amino beta-carbolines.

Authors:  Yohan Boursereau; Iain Coldham
Journal:  Bioorg Med Chem Lett       Date:  2004-12-06       Impact factor: 2.823

7.  Flazinamide, a novel beta-carboline compound with anti-HIV actions.

Authors:  Yun-Hua Wang; Jian-Guo Tang; Rui-Rui Wang; Liu-Meng Yang; Ze-Jun Dong; Li Du; Xu Shen; Ji-Kai Liu; Yong-Tang Zheng
Journal:  Biochem Biophys Res Commun       Date:  2007-02-23       Impact factor: 3.575

8.  Beta-carbolines: synthesis and neurochemical and pharmacological actions on brain benzodiazepine receptors.

Authors:  M Cain; R W Weber; F Guzman; J M Cook; S A Barker; K C Rice; J N Crawley; S M Paul; P Skolnick
Journal:  J Med Chem       Date:  1982-09       Impact factor: 7.446

9.  Synthesis of analogues of flazin, in particular, flazinamide, as promising anti-HIV agents.

Authors:  Jian-Guo Tang; Yun-Hua Wang; Rui-Rui Wang; Ze-Jun Dong; Liu-Meng Yang; Yong-Tang Zheng; Ji-Kai Liu
Journal:  Chem Biodivers       Date:  2008-03       Impact factor: 2.408

10.  Synthesis and in vitro cytotoxic evaluation of novel 3,4,5-trimethoxyphenyl substituted beta-carboline derivatives.

Authors:  Qifeng Wu; Rihui Cao; Manxiu Feng; Xiangdong Guan; Chunming Ma; Jinbing Liu; Huacan Song; Wenlie Peng
Journal:  Eur J Med Chem       Date:  2008-04-04       Impact factor: 6.514

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  7 in total

1.  Discovery and biological characterization of 1-(1H-indol-3-yl)-9H-pyrido[3,4-b]indole as an aryl hydrocarbon receptor activator generated by photoactivation of tryptophan by sunlight.

Authors:  Silvia Diani-Moore; Yuliang Ma; Erin Labitzke; Hui Tao; J David Warren; Jared Anderson; Qiuying Chen; Steven S Gross; Arleen B Rifkind
Journal:  Chem Biol Interact       Date:  2011-06-22       Impact factor: 5.192

2.  Efficient synthesis of eudistomin U and evaluation of its cytotoxicity.

Authors:  Chad M Roggero; Jennifer M Giulietti; Seann P Mulcahy
Journal:  Bioorg Med Chem Lett       Date:  2014-05-27       Impact factor: 2.823

3.  Three-step synthesis of an annulated β-carboline via palladium catalysis.

Authors:  Seann P Mulcahy; Jonathan G Varelas
Journal:  Tetrahedron Lett       Date:  2013-11-27       Impact factor: 2.415

4.  Cu-catalyzed mild and efficient oxidation of THβCs using air: application in practical total syntheses of perlolyrine and flazin.

Authors:  Bo Zheng; Tien Ha Trieu; Tian-Zhuo Meng; Xia Lu; Jing Dong; Qiang Zhang; Xiao-Xin Shi
Journal:  RSC Adv       Date:  2018-02-12       Impact factor: 4.036

5.  Total synthesis and biological activity of marine alkaloid Eudistomins Y1-Y7 and their analogues.

Authors:  Huijuan Jin; Puyong Zhang; Krikor Bijian; Sumei Ren; Shengbiao Wan; Moulay A Alaoui-Jamali; Tao Jiang
Journal:  Mar Drugs       Date:  2013-04-29       Impact factor: 5.118

Review 6.  IBX-Mediated Organic Transformations in Heterocyclic Chemistry-A Decade Update.

Authors:  Yadavalli Venkata Durga Nageswar; Katla Ramesh; Katla Rakhi
Journal:  Front Chem       Date:  2022-02-28       Impact factor: 5.221

Review 7.  Ascidian Toxins with Potential for Drug Development.

Authors:  Dianne J Watters
Journal:  Mar Drugs       Date:  2018-05-13       Impact factor: 5.118

  7 in total

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