Literature DB >> 20158219

Synthesis of 4-methyldienoates using a vinylogous Horner-Wadsworth-Emmons reagent. Application to the synthesis of trichostatic acid.

John T Markiewicz1, Douglas J Schauer, Joakim Löfstedt, Steven J Corden, Olaf Wiest, Paul Helquist.   

Abstract

The utility of the unsaturated phosphonate 1 as a vinylogous Horner-Wadsworth-Emmons reagent was explored in reactions with aldehydes affording 4-methyldienoate esters. Factors that affect E/Z selectivity were studied. A simplified synthesis of trichostatic acid 3 was accomplished to demonstrate utility of this reagent.

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Year:  2010        PMID： 20158219     DOI： 10.1021/jo902422y

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


  5 in total

1.  Approach to the Synthesis of the C1-C11 and C14-C18 portion of Leucascandrolide A.

Authors:  T J Hunter; J Zheng; G A O'Doherty
Journal:  Org Chem Front       Date:  2016-07-12       Impact factor: 5.281

2.  Regio- and stereospecific rhodium-catalyzed allylic alkylation with an acyl anion equivalent: an approach to acyclic α-ternary β,γ-unsaturated aryl ketones.

Authors:  Ben W H Turnbull; Jungha Chae; Samuel Oliver; P Andrew Evans
Journal:  Chem Sci       Date:  2017-03-31       Impact factor: 9.825

3.  First synthesis of novel 2,4-bis((E)-styryl)quinoline-3-carboxylate derivatives and their antitumor activity.

Authors:  Wentao Gao; Zhiyuan Li; Qiqi Xu; Yang Li
Journal:  RSC Adv       Date:  2018-11-19       Impact factor: 4.036

4.  Asymmetric total synthesis of a putative sex pheromone component from the parasitoid wasp Trichogramma turkestanica.

Authors:  Danny Geerdink; Jeffrey Buter; Teris A van Beek; Adriaan J Minnaard
Journal:  Beilstein J Org Chem       Date:  2014-04-02       Impact factor: 2.883

5.  Structure elucidation of female-specific volatiles released by the parasitoid wasp Trichogramma turkestanica (Hymenoptera: Trichogrammatidae).

Authors:  Armin Tröger; Teris A van Beek; Martinus E Huigens; Isabel M M S Silva; Maarten A Posthumus; Wittko Francke
Journal:  Beilstein J Org Chem       Date:  2014-04-02       Impact factor: 2.883
  5 in total

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