Literature DB >> 21135918

The application of (Z)-3-aryl-3-haloenoic acids to the synthesis of (Z)-5-benzylidene-4-arylpyrrol-2(5H)-ones.

John T Gupton1, Nakul Telang, Edith J Banner, Emily J Kluball, Kayleigh E Hall, Kara L Finzel, Xin Jia, Spencer R Bates, R Scott Welden, Benjamin C Giglio, James E Eaton, Peter J Barelli, Lauren T Firich, John A Stafford, Matthew B Coppock, Eric F Worrall, Rene P F Kanters, Kerry Keertikar, Rebecca Osterman.   

Abstract

Studies directed at the synthesis of (Z)-5-benzylidene-4-arylpyrrol-2(5H)-ones from (Z)-3-aryl-3-haloenoic acids are described. The successful strategy relies on the preparation of (Z)-3-aryl-3-haloenoic acids from acetophenones through the corresponding (Z)-3-aryl-3-haloenals and the conversion of the (Z)-3-aryl-3-haloenoic acids to (Z)-5-benzylidene-4-aryl-5H-furan-2-ones. The furanones were subsequently treated with primary amines and dehydrated to the corresponding (Z)-5-benzylidene-4-arylpyrrol-2(5H)-ones.

Entities:  

Year:  2010        PMID: 21135918      PMCID: PMC2997076          DOI: 10.1016/j.tet.2010.09.080

Source DB:  PubMed          Journal:  Tetrahedron        ISSN: 0040-4020            Impact factor:   2.457


  6 in total

1.  Baculiferins A-O, O-sulfated pyrrole alkaloids with anti-HIV-1 activity, from the Chinese marine sponge Iotrochota baculifera.

Authors:  Guotao Fan; Zelin Li; Shi Shen; Yi Zeng; Yishu Yang; Minjuang Xu; Torsten Bruhn; Heike Bruhn; Joachim Morschhäuser; Gerhard Bringmann; Wenhan Lin
Journal:  Bioorg Med Chem       Date:  2010-06-23       Impact factor: 3.641

2.  Total synthesis of ningalin D.

Authors:  Akiyuki Hamasaki; Jeffrey M Zimpleman; Inkyu Hwang; Dale L Boger
Journal:  J Am Chem Soc       Date:  2005-08-03       Impact factor: 15.419

3.  Ningalins A-D: Novel Aromatic Alkaloids from a Western Australian Ascidian of the Genus Didemnum.

Authors:  Heonjoong Kang; William Fenical
Journal:  J Org Chem       Date:  1997-05-16       Impact factor: 4.354

4.  The application of vinylogous iminium salt derivatives to efficient formal syntheses of the marine akaloids lamellarin G trimethyl ether and ningalin B.

Authors:  John T Gupton; Benjamin C Giglio; James E Eaton; Elizabeth A Rieck; Kristin L Smith; Matthew J Keough; Peter J Barelli; Lauren T Firich; Jonathan E Hempel; Timothy M Smith; Rene P F Kanters
Journal:  Tetrahedron       Date:  2009-05-30       Impact factor: 2.457

5.  Toward safer processes for C-C biaryl bond construction: catalytic direct C-H arylation and tin-free radical coupling in the synthesis of pyrazolophenanthridines.

Authors:  Susana Hernández; Isabel Moreno; Raul SanMartin; Germán Gómez; María Teresa Herrero; Esther Domínguez
Journal:  J Org Chem       Date:  2010-01-15       Impact factor: 4.354

6.  Multidrug resistance reversal activity of key ningalin analogues.

Authors:  Danielle R Soenen; Inkyu Hwang; Michael P Hedrick; Dale L Boger
Journal:  Bioorg Med Chem Lett       Date:  2003-05-19       Impact factor: 2.823

  6 in total

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