Literature DB >> 19555089

Palladium(II)-catalyzed cyclization of unsaturated hydroperoxides for the synthesis of 1,2-dioxanes.

Jason R Harris1, Shelli R Waetzig, K A Woerpel.   

Abstract

The cyclization of gamma,delta-unsaturated tertiary hydroperoxides in the presence of a palladium(II) catalyst afforded 1,2-dioxanes resembling biologically active natural products. A variety of substrates were screened, and synthetic manipulations were accomplished to construct compounds with structural similarity to antimalarial targets.

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Year:  2009        PMID： 19555089      PMCID： PMC2757105          DOI： 10.1021/ol901046z

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


  39 in total

1.  Synthesis of indolines and tetrahydroisoquinolines from arylethylamines by Pd(II)-catalyzed C-H activation reactions.

Authors:  Jiao-Jie Li; Tian-Sheng Mei; Jin-Quan Yu
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

2.  New readily accessible peroxides with high anti-malarial potency.

Authors:  Nobutoshi Murakami; Motoyuki Kawanishi; Sawako Itagaki; Toshihiro Horii; Motomasa Kobayashi
Journal:  Bioorg Med Chem Lett       Date:  2002-01-07       Impact factor: 2.823

3.  Total synthesis of peroxyacarnoates A and D: metal-mediated couplings as a convergent approach to polyunsaturated peroxides.

Authors:  Chunping Xu; Joseph M Raible; Patrick H Dussault
Journal:  Org Lett       Date:  2005-06-09       Impact factor: 6.005

4.  Palladium-catalyzed synthesis of N-aryl-2-benzylindolines via tandem arylation of 2-allylaniline: control of selectivity through in situ catalyst modification.

Authors:  Ricardo Lira; John P Wolfe
Journal:  J Am Chem Soc       Date:  2004-11-03       Impact factor: 15.419

Review 5.  Why artemisinin and certain synthetic peroxides are potent antimalarials. Implications for the mode of action.

Authors:  C W Jefford
Journal:  Curr Med Chem       Date:  2001-12       Impact factor: 4.530

6.  Palladium-catalyzed synthesis of N-aryl pyrrolidines from gamma-(N-Arylamino) alkenes: evidence for chemoselective alkene insertion into Pd--N bonds.

Authors:  Joshua E Ney; John P Wolfe
Journal:  Angew Chem Int Ed Engl       Date:  2004-07-05       Impact factor: 15.336

7.  Palladium-catalyzed highly stereoselective synthesis of N-aryl-3-arylmethylisoxazolidines via tandem arylation of O-homoallylhydroxylamines.

Authors:  Jinsong Peng; Wenqing Lin; Shixue Yuan; Yuanwei Chen
Journal:  J Org Chem       Date:  2007-03-17       Impact factor: 4.354

8.  Antifungal peroxyketal acids from an Okinawan marine sponge of Plakortis sp.

Authors:  M Kobayashi; K Kondo; I Kitagawa
Journal:  Chem Pharm Bull (Tokyo)       Date:  1993-07       Impact factor: 1.645

Review 9.  Natural peroxy anticancer agents.

Authors:  Valery M Dembitsky; Tatyana A Gloriozova; Vladimir V Poroikov
Journal:  Mini Rev Med Chem       Date:  2007-06       Impact factor: 3.862

Review 10.  Qinghaosu (artemisinin): an antimalarial drug from China.

Authors:  D L Klayman
Journal:  Science       Date:  1985-05-31       Impact factor: 47.728
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  10 in total

1.  Cu(II)-catalyzed aerobic hydroperoxidation of Meldrum's acid derivatives and application in intramolecular oxidation: a conceptual blueprint for O2/H2 dihydroxylation.

Authors:  Scott W Krabbe; Dung T Do; Jeffrey S Johnson
Journal:  Org Lett       Date:  2012-11-19       Impact factor: 6.005

2.  Endoperoxide synthesis by photocatalytic aerobic [2 + 2 + 2] cycloadditions.

Authors:  Jonathan D Parrish; Michael A Ischay; Zhan Lu; Song Guo; Noël R Peters; Tehshik P Yoon
Journal:  Org Lett       Date:  2012-02-28       Impact factor: 6.005

3.  Catalytic Enantioselective Peroxidation of α,β-Unsaturated Aldehydes for the Asymmetric Synthesis of Biologically Important Chiral Endoperoxides.

Authors:  Lin Hu; Xiaojie Lu; Li Deng
Journal:  J Am Chem Soc       Date:  2015-06-29       Impact factor: 15.419

4.  Asymmetric Synthesis of 1,2-dioxanes: Approaches to the Peroxyplakoric Acids.

Authors:  Chunping Xu; Chris Schwartz; Joseph Raible; Patrick H Dussault
Journal:  Tetrahedron       Date:  2009-11-21       Impact factor: 2.457

Review 5.  Lewis Acids and Heteropoly Acids in the Synthesis of Organic Peroxides.

Authors:  Ivan A Yaremenko; Peter S Radulov; Yulia Yu Belyakova; Dmitriy I Fomenkov; Svetlana B Tsogoeva; Alexander O Terent'ev
Journal:  Pharmaceuticals (Basel)       Date:  2022-04-13

6.  Palladium-Catalyzed Enantioselective Intermolecular Coupling of Phenols and Allylic Alcohols.

Authors:  Nicholas J Race; Cristiane S Schwalm; Takayuki Nakamuro; Matthew S Sigman
Journal:  J Am Chem Soc       Date:  2016-12-01       Impact factor: 15.419

Review 7.  Synthesis of five- and six-membered cyclic organic peroxides: Key transformations into peroxide ring-retaining products.

Authors:  Alexander O Terent'ev; Dmitry A Borisov; Vera A Vil'; Valery M Dembitsky
Journal:  Beilstein J Org Chem       Date:  2014-01-08       Impact factor: 2.883

Review 8.  Structural basis for endoperoxide-forming oxygenases.

Authors:  Takahiro Mori; Ikuro Abe
Journal:  Beilstein J Org Chem       Date:  2022-06-21       Impact factor: 2.544

9.  Nox4-dependent ROS modulation by amino endoperoxides to induce apoptosis in cancer cells.

Authors:  P Zhu; B M K Tong; R Wang; J P Chen; S Foo; H C Chong; X L Wang; G Y Ang; S Chiba; N S Tan
Journal:  Cell Death Dis       Date:  2013-03-21       Impact factor: 8.469

10.  Cyclization-endoperoxidation cascade reactions of dienes mediated by a pyrylium photoredox catalyst.

Authors:  Nathan J Gesmundo; David A Nicewicz
Journal:  Beilstein J Org Chem       Date:  2014-06-03       Impact factor: 2.883
  10 in total

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