Literature DB >> 23055437

Concise syntheses of insect pheromones using Z-selective cross metathesis.

Myles B Herbert1, Vanessa M Marx, Richard L Pederson, Robert H Grubbs.   

Abstract

Very short synthetic routes to nine cis-olefin-containing pheromones containing a variety of functionality, including an unconjugated (E,Z) diene, are reported. These lepidopteran pheromones are used extensively for pest control, and were easily prepared using ruthenium-based Z-selective cross metathesis, highlighting the advantages of this method over less efficient ways to form Z olefins.
Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

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Year:  2012        PMID： 23055437      PMCID： PMC3789658          DOI： 10.1002/anie.201206079

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


  13 in total

1.  Potential for use of synthetic sex pheromone for mating disruption of the olive pyralid moth, Euzophera pinguis.

Authors:  Antonio Ortiz; Antonio Quesada; Adolfo Sanchez
Journal:  J Chem Ecol       Date:  2004-05       Impact factor: 2.626

2.  Enantiodivergent synthesis of both enantiomers of gypsy moth pheromone disparlure.

Authors:  Kavirayani R Prasad; Pazhamalai Anbarasan
Journal:  J Org Chem       Date:  2007-03-17       Impact factor: 4.354

Review 3.  Plant oil renewable resources as green alternatives in polymer science.

Authors:  Michael A R Meier; Jürgen O Metzger; Ulrich S Schubert
Journal:  Chem Soc Rev       Date:  2007-11       Impact factor: 54.564

4.  Chelated ruthenium catalysts for Z-selective olefin metathesis.

Authors:  Koji Endo; Robert H Grubbs
Journal:  J Am Chem Soc       Date:  2011-05-12       Impact factor: 15.419

5.  Z-selective metathesis homocoupling of 1,3-dienes by molybdenum and tungsten monoaryloxide pyrrolide (MAP) complexes.

Authors:  Erik M Townsend; Richard R Schrock; Amir H Hoveyda
Journal:  J Am Chem Soc       Date:  2012-07-02       Impact factor: 15.419

6.  Z-selective homodimerization of terminal olefins with a ruthenium metathesis catalyst.

Authors:  Benjamin K Keitz; Koji Endo; Myles B Herbert; Robert H Grubbs
Journal:  J Am Chem Soc       Date:  2011-06-08       Impact factor: 15.419

7.  Isolation of pure disubstituted E olefins through Mo-catalyzed Z-selective ethenolysis of stereoisomeric mixtures.

Authors:  Smaranda C Marinescu; Daniel S Levine; Yu Zhao; Richard R Schrock; Amir H Hoveyda
Journal:  J Am Chem Soc       Date:  2011-07-07       Impact factor: 15.419

8.  Cis-selective ring-opening metathesis polymerization with ruthenium catalysts.

Authors:  Benjamin K Keitz; Alexey Fedorov; Robert H Grubbs
Journal:  J Am Chem Soc       Date:  2012-01-20       Impact factor: 15.419

9.  Chemoselective construction of substituted conjugated dienes using an olefin cross-metathesis protocol.

Authors:  Timothy W Funk; Jon Efskind; Robert H Grubbs
Journal:  Org Lett       Date:  2005-01-20       Impact factor: 6.005

10.  Sunflower-based feedstocks in nonfood applications: Perspectives from olefin metathesis.

Authors:  Bassie B Marvey
Journal:  Int J Mol Sci       Date:  2008-08-13       Impact factor: 6.208
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  27 in total

1.  Synthesis of Linear (Z)-α,β-Unsaturated Esters by Catalytic Cross-Metathesis. The Influence of Acetonitrile.

Authors:  Elsie C Yu; Brett M Johnson; Erik M Townsend; Richard R Schrock; Amir H Hoveyda
Journal:  Angew Chem Int Ed Engl       Date:  2016-10-10       Impact factor: 15.336

2.  Traceless Protection for More Broadly Applicable Olefin Metathesis.

Authors:  Yucheng Mu; Thach T Nguyen; Farid W van der Mei; Richard R Schrock; Amir H Hoveyda
Journal:  Angew Chem Int Ed Engl       Date:  2019-03-13       Impact factor: 15.336

3.  Ru-Based Z-Selective Metathesis Catalysts with Modified Cyclometalated Carbene Ligands.

Authors:  Sarah M Bronner; Myles B Herbert; Paresma R Patel; Vanessa M Marx; Robert H Grubbs
Journal:  Chem Sci       Date:  2014-10       Impact factor: 9.825

Review 4.  Recent advances in ruthenium-based olefin metathesis.

Authors:  O M Ogba; N C Warner; D J O'Leary; R H Grubbs
Journal:  Chem Soc Rev       Date:  2018-06-18       Impact factor: 54.564

5.  Synthesis of (+)-Disparlure via Enantioselective Iodolactonization.

Authors:  Daniel W Klosowski; Stephen F Martin
Journal:  Org Lett       Date:  2018-02-12       Impact factor: 6.005

6.  Palladium-Catalyzed Decarbonylative Dehydration of Fatty Acids for the Production of Linear Alpha Olefins.

Authors:  Yiyang Liu; Kelly E Kim; Myles B Herbert; Alexey Fedorov; Robert H Grubbs; Brian M Stoltz
Journal:  Adv Synth Catal       Date:  2014-01-01       Impact factor: 5.837

7.  Catalytic, enantioselective synthesis of 1,2-anti-diols by asymmetric ring-opening/cross-metathesis.

Authors:  John Hartung; Robert H Grubbs
Journal:  Angew Chem Int Ed Engl       Date:  2014-02-19       Impact factor: 15.336

8.  Z-Selective Ruthenium Metathesis Catalysts: Comparison of Nitrate and Nitrite X-type Ligands.

Authors:  Melanie A Pribisko; Tonia S Ahmed; Robert H Grubbs
Journal:  Polyhedron       Date:  2014-12-14       Impact factor: 3.052

9.  Stereoselective access to Z and E macrocycles by ruthenium-catalyzed Z-selective ring-closing metathesis and ethenolysis.

Authors:  Vanessa M Marx; Myles B Herbert; Benjamin K Keitz; Robert H Grubbs
Journal:  J Am Chem Soc       Date:  2012-12-21       Impact factor: 15.419

10.  Highly active ruthenium metathesis catalysts exhibiting unprecedented activity and Z-selectivity.

Authors:  Lauren E Rosebrugh; Myles B Herbert; Vanessa M Marx; Benjamin K Keitz; Robert H Grubbs
Journal:  J Am Chem Soc       Date:  2013-01-17       Impact factor: 15.419
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