Literature DB >> 21405073

Direct conversion of benzylic and allylic alcohols to phosphonates.

Rocky J Barney1, Rebekah M Richardson, David F Wiemer.   

Abstract

Benzyl phosphonate esters often serve as reagents in Horner-Wadsworth-Emmons reactions. In most cases, they can be prepared from pan class="Chemical">benzylic alcohols via formation of the corresponding halide followed by an Arbuzov reaction. To identify a more direct synthesis of phosphonate esters, we have developed a one-flask procedure for conversion of benzylic and allylic alcohols to the corresponding phosphonates through treatment with triethyl phosphite and ZnI(2).

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Year:  2011        PMID: 21405073      PMCID: PMC3204863          DOI: 10.1021/jo200137k

Source DB:  PubMed          Journal:  J Org Chem        ISSN: 0022-3263            Impact factor:   4.354


  20 in total

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2.  Synthesis of nonracemic 3-deoxyschweinfurthin B.

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3.  Cytotoxic geranyl stilbenes from Macaranga schweinfurthii.

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4.  Novel limonene phosphonate and farnesyl diphosphate analogues: design, synthesis, and evaluation as potential protein-farnesyl transferase inhibitors.

Authors:  J T Eummer; B S Gibbs; T J Zahn; J S Sebolt-Leopold; R A Gibbs
Journal:  Bioorg Med Chem       Date:  1999-02       Impact factor: 3.641

5.  Antiproliferative prenylated stilbenes and flavonoids from Macaranga alnifolia from the Madagascar rainforest.

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Journal:  J Nat Prod       Date:  2007-02-28       Impact factor: 4.050

6.  Total synthesis of (R,R,R)- and (S,S,S)-schweinfurthin F: differences of bioactivity in the enantiomeric series.

Authors:  Nolan R Mente; Andrew J Wiemer; Jeffrey D Neighbors; John A Beutler; Raymond J Hohl; David F Wiemer
Journal:  Bioorg Med Chem Lett       Date:  2006-12-12       Impact factor: 2.823

7.  Total synthesis of (+)-schweinfurthins B and E.

Authors:  Joseph J Topczewski; Jeffrey D Neighbors; David F Wiemer
Journal:  J Org Chem       Date:  2009-09-18       Impact factor: 4.354

8.  BF3 x Et2O-mediated cascade cyclizations: synthesis of schweinfurthins F and G.

Authors:  Nolan R Mente; Jeffrey D Neighbors; David F Wiemer
Journal:  J Org Chem       Date:  2008-09-17       Impact factor: 4.354

9.  A concise synthesis of pawhuskin A.

Authors:  Jeffrey D Neighbors; Matthew J Buller; Kelly D Boss; David F Wiemer
Journal:  J Nat Prod       Date:  2008-10-15       Impact factor: 4.050

10.  Alpha-phosphono lactone analogues of farnesyl pyrophosphate: an asymmetric synthesis via ring-closing metathesis.

Authors:  Yanming Du; David F Wiemer
Journal:  J Org Chem       Date:  2002-08-09       Impact factor: 4.354

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  6 in total

1.  Synthesis of α-Arylphosphonates Using Copper-Catalyzed α-Arylation and Deacylative α-Arylation of β-Ketophosphonates.

Authors:  Laxmidhar Rout; Sridhar Regati; Cong-Gui Zhao
Journal:  Adv Synth Catal       Date:  2011-12-06       Impact factor: 5.837

2.  Synthesis and reactivity of alkyl-1,1,1-trisphosphonate esters.

Authors:  Jacqueline P Smits; David F Wiemer
Journal:  J Org Chem       Date:  2011-10-04       Impact factor: 4.354

3.  First DMAP-mediated direct conversion of Morita-Baylis-Hillman alcohols into γ-ketoallylphosphonates: Synthesis of γ-aminoallylphosphonates.

Authors:  Marwa Ayadi; Haitham Elleuch; Emmanuel Vrancken; Farhat Rezgui
Journal:  Beilstein J Org Chem       Date:  2016-12-30       Impact factor: 2.883

Review 4.  Polymer-Supported Phosphoric, Phosphonic and Phosphinic Acids-From Synthesis to Properties and Applications in Separation Processes.

Authors:  Agnieszka Głowińska; Andrzej W Trochimczuk
Journal:  Molecules       Date:  2020-09-15       Impact factor: 4.411

5.  Synthesis of a Coumarin-Based Analogue of Schweinfurthin F.

Authors:  Chloe M Schroeder; Patrick N Dey; John A Beutler; David F Wiemer
Journal:  J Org Chem       Date:  2021-10-29       Impact factor: 4.354

Review 6.  Improvements, Variations and Biomedical Applications of the Michaelis-Arbuzov Reaction.

Authors:  Stavroula Kostoudi; Georgios Pampalakis
Journal:  Int J Mol Sci       Date:  2022-03-21       Impact factor: 5.923

  6 in total

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