Literature DB >> 21306121

Reductive cyclization cascades of lactones using SmI2-H2O.

Dixit Parmar1, Kieran Price, Malcolm Spain, Hiroshi Matsubara, Paul A Bradley, David J Procter.   

Abstract

Lactones bearing two alkenes or an alkene and an alkyne undergo reductive cyclization cascades upon treatment with SmI(2)-H(2)O, giving decorated azulene motifs in excellent yields with good diastereocontrol.

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Year:  2011        PMID： 21306121     DOI： 10.1021/ja1114908

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  11 in total

1.  Selective synthesis of 3-hydroxy acids from Meldrum's acids using SmI2-H2O.

Authors:  Michal Szostak; Malcolm Spain; David J Procter
Journal:  Nat Protoc       Date:  2012-04-26       Impact factor: 13.491

2.  Synthesis and Utility of Dihydropyridine Boronic Esters.

Authors:  Santanu Panda; Aaron Coffin; Q Nhu Nguyen; Dean J Tantillo; Joseph M Ready
Journal:  Angew Chem Int Ed Engl       Date:  2015-12-22       Impact factor: 15.336

3.  Overturning established chemoselectivities: selective reduction of arenes over malonates and cyanoacetates by photoactivated organic electron donors.

Authors:  Eswararao Doni; Bhaskar Mondal; Steven O'Sullivan; Tell Tuttle; John A Murphy
Journal:  J Am Chem Soc       Date:  2013-07-19       Impact factor: 15.419

4.  Selective reduction of barbituric acids using SmI2/H2O: synthesis, reactivity, and structural analysis of tetrahedral adducts.

Authors:  Michal Szostak; Brice Sautier; Malcolm Spain; Maike Behlendorf; David J Procter
Journal:  Angew Chem Int Ed Engl       Date:  2013-10-09       Impact factor: 15.336

5.  Uncovering the importance of proton donors in TmI2-promoted electron transfer: facile C-N bond cleavage in unactivated amides.

Authors:  Michal Szostak; Malcolm Spain; David J Procter
Journal:  Angew Chem Int Ed Engl       Date:  2013-06-12       Impact factor: 15.336

6.  Selective Synthesis of Cyclooctanoids by Radical Cyclization of Seven-Membered Lactones: Neutron Diffraction Study of the Stereoselective Deuteration of a Chiral Organosamarium Intermediate.

Authors:  Xavier Just-Baringo; Jemma Clark; Matthias J Gutmann; David J Procter
Journal:  Angew Chem Int Ed Engl       Date:  2016-09-07       Impact factor: 15.336

7.  Copper-Catalyzed Double Additions and Radical Cyclization Cascades in the Re-Engineering of the Antibacterial Pleuromutilin.

Authors:  Rebecca E Ruscoe; Neal J Fazakerley; Huanming Huang; Sabine Flitsch; David J Procter
Journal:  Chemistry       Date:  2015-11-26       Impact factor: 5.236

8.  Biocatalytic Conversion of Cyclic Ketones Bearing α-Quaternary Stereocenters into Lactones in an Enantioselective Radical Approach to Medium-Sized Carbocycles.

Authors:  Charlotte Morrill; Chantel Jensen; Xavier Just-Baringo; Gideon Grogan; Nicholas J Turner; David J Procter
Journal:  Angew Chem Int Ed Engl       Date:  2018-03-05       Impact factor: 15.336

Review 9.  Synthesis of Nitrogen Heterocycles Using Samarium(II) Iodide.

Authors:  Shicheng Shi; Michal Szostak
Journal:  Molecules       Date:  2017-11-21       Impact factor: 4.411

10.  Samarium(II) folding cascades involving hydrogen atom transfer for the synthesis of complex polycycles.

Authors:  Mateusz P Plesniak; Monserrat H Garduño-Castro; Philipp Lenz; Xavier Just-Baringo; David J Procter
Journal:  Nat Commun       Date:  2018-11-15       Impact factor: 14.919
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