Literature DB >> 20222691

A divergent approach to the diastereoselective synthesis of several ant-associated iridoids.

Joel S Beckett1, James D Beckett, John E Hofferberth.   

Abstract

The ant-associated iridoids nepetalactol, actinidine, dolichodial, isoiridomyrmecin, and dihydronepetalactone were prepared from citronellal using a divergent approach. Key features include a three-step synthesis of the individual antipodes of actinidine by a novel tandem cycloaddition/pyridine formation and a facile diastereoselective synthesis of both enantiomers of dolichodial.

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Year:  2010        PMID： 20222691     DOI： 10.1021/ol100077z

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  9 in total

1.  Stereoselective chemical defense in the Drosophila parasitoid Leptopilina heterotoma is mediated by (-)-iridomyrmecin and (+)-isoiridomyrmecin.

Authors:  Johannes Stökl; John Hofferberth; Maria Pritschet; Michael Brummer; Joachim Ruther
Journal:  J Chem Ecol       Date:  2012-04-05       Impact factor: 2.626

2.  Synthesis and biological analysis of truncated calyculone H.

Authors:  Penagaluri Balasubramanyam; Abimael D Rodríguez
Journal:  Tetrahedron       Date:  2017-01-14       Impact factor: 2.457

3.  Nature-inspired total synthesis of (-)-fusarisetin A.

Authors:  Jing Xu; Eduardo J E Caro-Diaz; Lynnie Trzoss; Emmanuel A Theodorakis
Journal:  J Am Chem Soc       Date:  2012-03-08       Impact factor: 15.419

4.  Behavioral differences among domestic cats in the response to cat-attracting plants and their volatile compounds reveal a potential distinct mechanism of action for actinidine.

Authors:  Sebastiaan Bol; Adrian Scaffidi; Evelien M Bunnik; Gavin R Flematti
Journal:  BMC Biol       Date:  2022-08-25       Impact factor: 7.364

5.  Stereoselective synthesis of trans-fused iridoid lactones and their identification in the parasitoid wasp Alloxysta victrix, Part I: Dihydronepetalactones.

Authors:  Nicole Zimmermann; Robert Hilgraf; Lutz Lehmann; Daniel Ibarra; Wittko Francke
Journal:  Beilstein J Org Chem       Date:  2012-08-07       Impact factor: 2.883

6.  Stereoselective synthesis of trans-fused iridoid lactones and their identification in the parasitoid wasp Alloxysta victrix, Part II: Iridomyrmecins.

Authors:  Robert Hilgraf; Nicole Zimmermann; Lutz Lehmann; Armin Tröger; Wittko Francke
Journal:  Beilstein J Org Chem       Date:  2012-08-08       Impact factor: 2.883

7.  Characterization of 10-hydroxygeraniol dehydrogenase from Catharanthus roseus reveals cascaded enzymatic activity in iridoid biosynthesis.

Authors:  Ramakrishnan Krithika; Prabhakar Lal Srivastava; Bajaj Rani; Swati P Kolet; Manojkumar Chopade; Mantri Soniya; Hirekodathakallu V Thulasiram
Journal:  Sci Rep       Date:  2015-02-05       Impact factor: 4.379

8.  Chemoselective and one-pot synthesis of novel coumarin-based cyclopenta[c]pyrans via base-mediated reaction of α,β-unsaturated coumarins and β-ketodinitriles.

Authors:  Behnaz Farajpour; Abdolali Alizadeh
Journal:  RSC Adv       Date:  2022-03-04       Impact factor: 3.361

9.  Drosophila Avoids Parasitoids by Sensing Their Semiochemicals via a Dedicated Olfactory Circuit.

Authors:  Shimaa A M Ebrahim; Hany K M Dweck; Johannes Stökl; John E Hofferberth; Federica Trona; Kerstin Weniger; Jürgen Rybak; Yoichi Seki; Marcus C Stensmyr; Silke Sachse; Bill S Hansson; Markus Knaden
Journal:  PLoS Biol       Date:  2015-12-16       Impact factor: 8.029
  9 in total

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