Literature DB >> 23780558

Stereoselective syntheses of functionalized spirocyclopenteneoxindoles via triphenylphosphine-catalyzed [3+2] cycloaddition reactions.

Qing-Fa Zhou1, Xue-Ping Chu, Fei-Fei Ge, Cheng Li, Tao Lu.   

Abstract

Spirocyclopenteneoxindole derivatives were obtained by stereoselective triphenylphosphine-catalyzed [3+2] cycloadditions of ynones and alkylidene oxindole derivatives. This approach is based on the Michael addition of ynones to alkylidene oxindole derivatives, followed by intermolecular [Formula: see text]-addition using 50 mol% triphenylphosphine as catalyst.

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Year:  2013        PMID： 23780558     DOI： 10.1007/s11030-013-9456-8

Source DB:  PubMed          Journal:  Mol Divers        ISSN： 1381-1991            Impact factor:   2.943


  32 in total

1.  A Rapid Total Synthesis of Spirotryprostatin B: Proof of Its Relative and Absolute Stereochemistry F.v.N. gratefully acknowledges the Alexander-von-Humboldt-Stiftung for a Feodor-Lynen fellowship that was kindly backed by Dr. R. Breslow as second host. This research was supported by the National Institutes of Health (Grant number HL 25848). We thank Dr. H. Osada (RIKEN) for providing us with spectra of the natural product. Furthermore we are grateful to Dr. D. Lichtblau from the Nakanishi laboratory for help with the CD spectra. We acknowledge the collaborative efforts of Ms. Maria Manzoni in these studies.

Authors: 
Journal:  Angew Chem Int Ed Engl       Date:  2000-06-16       Impact factor: 15.336

2.  Enantioselective synthesis of 3,3'-dihydropyrryl-spirooxindoles via an organocatalytic three-component reaction.

Authors:  Wen-Tao Wei; Chun-Xia Chen; Rui-Jiong Lu; Jin-Jia Wang; Xue-Jing Zhang; Ming Yan
Journal:  Org Biomol Chem       Date:  2012-06-11       Impact factor: 3.876

3.  Design, synthesis and biological evaluations of novel oxindoles as HIV-1 non-nucleoside reverse transcriptase inhibitors. Part I.

Authors:  Tao Jiang; Kelli L Kuhen; Karen Wolff; Hong Yin; Kimberly Bieza; Jeremy Caldwell; Badry Bursulaya; Tom Yao-Hsing Wu; Yun He
Journal:  Bioorg Med Chem Lett       Date:  2006-02-09       Impact factor: 2.823

4.  Isolation, structure elucidation, and biomimetic total synthesis of versicolamide B, and the isolation of antipodal (-)-stephacidin A and (+)-notoamide B from Aspergillus versicolor NRRL 35600.

Authors:  Thomas J Greshock; Alan W Grubbs; Ping Jiao; Donald T Wicklow; James B Gloer; Robert M Williams
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

5.  Asymmetric quadruple aminocatalytic domino reactions to fused carbocycles incorporating a spirooxindole motif.

Authors:  Kun Jiang; Zhi-Jun Jia; Xiang Yin; Li Wu; Ying-Chun Chen
Journal:  Org Lett       Date:  2010-06-18       Impact factor: 6.005

6.  Reactions of electron-deficient alkynes and allenes under phosphine catalysis.

Authors:  X Lu; C Zhang; Z Xu
Journal:  Acc Chem Res       Date:  2001-07       Impact factor: 22.384

7.  Serine derived NK1 antagonists. 2: A pharmacophore model for arylsulfonamide binding.

Authors:  J M Elliott; H Broughton; M A Cascieri; G Chicchi; I T Huscroft; M Kurtz; A M MacLeod; S Sadowski; G I Stevenson
Journal:  Bioorg Med Chem Lett       Date:  1998-07-21       Impact factor: 2.823

Review 8.  Pyrrolidinyl-spirooxindole natural products as inspirations for the development of potential therapeutic agents.

Authors:  Chris V Galliford; Karl A Scheidt
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

Review 9.  Strategies for the enantioselective synthesis of spirooxindoles.

Authors:  Nicolas R Ball-Jones; Joseph J Badillo; Annaliese K Franz
Journal:  Org Biomol Chem       Date:  2012-05-14       Impact factor: 3.876

10.  Asymmetric pericyclic cascade approach to spirocyclic oxindoles.

Authors:  Edward Richmond; Nicolas Duguet; Alexandra M Z Slawin; Tomáš Lébl; Andrew D Smith
Journal:  Org Lett       Date:  2012-05-14       Impact factor: 6.005
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  4 in total

1.  A synthesis of fused acenaphthopyrrolizines via the 1,3-dipolar cycloaddition reaction of azomethine ylides with acetylenic esters.

Authors:  Issa Yavari; Leila Baoosi; Mohammad R Halvagar
Journal:  Mol Divers       Date:  2017-01-13       Impact factor: 2.943

2.  Stereoselective Syntheses of α,β-Unsaturated γ-Amino Esters Through Phosphine-Catalyzed γ-Umpolung Additions of Sulfonamides to γ-Substituted Allenoates.

Authors:  Qing-Fa Zhou; Kui Zhang; Ohyun Kwon
Journal:  Tetrahedron Lett       Date:  2015-06-03       Impact factor: 2.415

Review 3.  Phosphine Organocatalysis.

Authors:  Hongchao Guo; Yi Chiao Fan; Zhanhu Sun; Yang Wu; Ohyun Kwon
Journal:  Chem Rev       Date:  2018-09-27       Impact factor: 60.622

4.  Phosphine-Catalyzed Intramolecular Cyclizations of α-Nitroethylallenoates Forming (Z)-Furanone Oximes.

Authors:  Qing-Fa Zhou; Kui Zhang; Lingchao Cai; Ohyun Kwon
Journal:  Org Lett       Date:  2016-05-27       Impact factor: 6.005
  4 in total

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