Literature DB >> 20160918

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

Chunping Xu1, Chris Schwartz, Joseph Raible, Patrick H Dussault.   

Abstract

The stereospecific intramolecular alkylation of a hydroperoxyacetal provides the basis for the first asymmetric synthesis of the dioxane propionate core of the peroxyplakorates. Chemoselective hydrometallation of an alkyne in the presence of a peroxide is used to introduce a synthon for the polyunsaturated side chains of the peroxyplakorates. The route suggests a general solution for the 1,2-dioxane unit in many peroxide natural products.

Entities:  

Year:  2009        PMID： 20160918      PMCID： PMC2770270          DOI： 10.1016/j.tet.2009.09.068

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


  16 in total

Review 1.  Peroxy natural products.

Authors:  D A Casteel
Journal:  Nat Prod Rep       Date:  1992-08       Impact factor: 13.423

2.  Catalytic enantioselective peroxidation of alpha,beta-unsaturated ketones.

Authors:  Xiaojie Lu; Yan Liu; Bingfeng Sun; Brittany Cindric; Li Deng
Journal:  J Am Chem Soc       Date:  2008-06-05       Impact factor: 15.419

3.  Intramolecular reactions of hydroperoxides and oxetanes: stereoselective synthesis of 1,2-dioxolanes and 1,2-dioxanes.

Authors:  Peng Dai; Patrick H Dussault
Journal:  Org Lett       Date:  2005-09-29       Impact factor: 6.005

4.  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

5.  Total Synthesis of the Alkoxydioxines (+)- and (-)-Chondrillin and (+)- and (-)-Plakorin via Singlet Oxygenation/Radical Rearrangement.

Authors:  Patrick H. Dussault; C. Todd Eary; Kevin R. Woller
Journal:  J Org Chem       Date:  1999-03-19       Impact factor: 4.354

6.  Boron-mediated aldol reaction of carboxylic esters: complementary anti- and syn-selective asymmetric aldol reactions.

Authors:  Tadashi Inoue; Ji-Feng Liu; Dana C Buske; Atsushi Abiko
Journal:  J Org Chem       Date:  2002-07-26       Impact factor: 4.354

7.  Boron-mediated aldol reaction of carboxylic esters.

Authors:  Atsushi Abiko
Journal:  Acc Chem Res       Date:  2004-06       Impact factor: 22.384

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

9.  First total synthesis of natural 6-epiplakortolide e.

Authors:  Mankil Jung; Jungyeob Ham; Jueun Song
Journal:  Org Lett       Date:  2002-08-08       Impact factor: 6.005

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

Authors:  Jason R Harris; Shelli R Waetzig; K A Woerpel
Journal:  Org Lett       Date:  2009-08-06       Impact factor: 6.005
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  4 in total

1.  Synthesis of antitrypanosomal 1,2-dioxane derivatives based on a natural product scaffold.

Authors:  Harish Holla; Mehdi Labaied; Ngoc Pham; Ian D Jenkins; Kenneth Stuart; Ronald J Quinn
Journal:  Bioorg Med Chem Lett       Date:  2011-07-13       Impact factor: 2.823

2.  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

Review 3.  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 4.  Peroxides with Anthelmintic, Antiprotozoal, Fungicidal and Antiviral Bioactivity: Properties, Synthesis and Reactions.

Authors:  Vera A Vil'; Ivan A Yaremenko; Alexey I Ilovaisky; Alexander O Terent'ev
Journal:  Molecules       Date:  2017-11-02       Impact factor: 4.411
  4 in total

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