Literature DB >> 27273761

Scalable procedure for the fragmentation of hydroperoxides mediated by copper and iron tetrafluoroborate salts.

David Huang1, Alexander W Schuppe, Michael Z Liang, Timothy R Newhouse.   

Abstract

An improved protocol for the formal elimination of propene from organic substrates is reported. This process entails the ozonolytic conversion of an alkene to a methoxy hydroperoxide which undergoes fragmentation mediated by copper and iron. The use of soluble Cu(BF4)2 and Fe(BF4)2 results in reproducible results up to a 100 gram scale.

Entities:  

Year:  2016        PMID： 27273761      PMCID： PMC5111968          DOI： 10.1039/c6ob00941g

Source DB:  PubMed          Journal:  Org Biomol Chem        ISSN： 1477-0520            Impact factor:   3.876


  6 in total

1.  Structure confirmation of a bioactive lactone isolated from Otoba parvifolia through the synthesis of a model compound.

Authors:  Francisco A Marques; Cesar A Lenz; Fabio Simonelli; Beatriz Helena L Noronha Sales Maia; Adriana P Vellasco; Marcos N Eberlin
Journal:  J Nat Prod       Date:  2004-11       Impact factor: 4.050

2.  Tunneling in tocopherol-mediated peroxidation of 7-dehydrocholesterol.

Authors:  H Muchalski; L Xu; N A Porter
Journal:  Org Biomol Chem       Date:  2014-12-01       Impact factor: 3.876

3.  Total synthesis of (+)-pleuromutilin.

Authors:  Neal J Fazakerley; Matthew D Helm; David J Procter
Journal:  Chemistry       Date:  2013-04-15       Impact factor: 5.236

4.  Biomimetic synthesis of 5,6-dihydro-glaucogenin C: construction of the disecopregnane skeleton by iron(II)-promoted fragmentation of an α-alkoxy hydroperoxide.

Authors:  Jinghan Gui; Dahai Wang; Weisheng Tian
Journal:  Angew Chem Int Ed Engl       Date:  2011-06-17       Impact factor: 15.336

5.  Engineering an antibiotic to fight cancer: optimization of the novobiocin scaffold to produce anti-proliferative agents.

Authors:  Huiping Zhao; Alison C Donnelly; Bhaskar R Kusuma; Gary E L Brandt; Douglas Brown; Roger A Rajewski; George Vielhauer; Jeffrey Holzbeierlein; Mark S Cohen; Brian S J Blagg
Journal:  J Med Chem       Date:  2011-05-09       Impact factor: 7.446

6.  Enantiospecific total synthesis of (-)-bakkenolide III and formal total synthesis of (-)-bakkenolides B, C, H, L, V, and X.

Authors:  Chiao-Hua Jiang; Annyt Bhattacharyya; Chin-Kang Sha
Journal:  Org Lett       Date:  2007-07-24       Impact factor: 6.005
  6 in total
  6 in total

1.  Carvone-Derived P-Stereogenic Phosphines: Design, Synthesis, and Use in Allene-Imine [3 + 2] Annulation.

Authors:  Andrew J Smaligo; Sriramurthy Vardhineedi; Ohyun Kwon
Journal:  ACS Catal       Date:  2018-05-04       Impact factor: 13.084

2.  Oxodealkenylative Cleavage of Alkene C(sp3 )-C(sp2 ) Bonds: A Practical Method for Introducing Carbonyls into Chiral Pool Materials.

Authors:  Andrew J Smaligo; Jason Wu; Nikolas R Burton; Allison S Hacker; Aslam C Shaikh; Jason C Quintana; Ruoxi Wang; Changmin Xie; Ohyun Kwon
Journal:  Angew Chem Int Ed Engl       Date:  2019-12-02       Impact factor: 15.336

3.  Assembly of the Limonoid Architecture by a Divergent Approach: Total Synthesis of (±)-Andirolide N via (±)-8α-Hydroxycarapin.

Authors:  Alexander W Schuppe; Timothy R Newhouse
Journal:  J Am Chem Soc       Date:  2017-01-05       Impact factor: 15.419

4.  Dealkenylative Thiylation of C(sp3)-C(sp2) Bonds.

Authors:  Andrew J Smaligo; Ohyun Kwon
Journal:  Org Lett       Date:  2019-10-01       Impact factor: 6.005

5.  Dealkenylative Alkenylation: Formal σ-Bond Metathesis of Olefins.

Authors:  Manisha Swain; Gusein Sadykhov; Ruoxi Wang; Ohyun Kwon
Journal:  Angew Chem Int Ed Engl       Date:  2020-08-28       Impact factor: 15.336

Review 6.  Recent Achievements in Total Synthesis for Integral Structural Revisions of Marine Natural Products.

Authors:  Min Woo Ha; Jonghoon Kim; Seung-Mann Paek
Journal:  Mar Drugs       Date:  2022-02-25       Impact factor: 5.118
  6 in total

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