Literature DB >> 16011337

An iterative catalytic route to enantiopure deoxypropionate subunits: asymmetric conjugate addition of grignard reagents to alpha,beta-unsaturated thioesters.

Renaud Des Mazery1, Maddalena Pullez, Fernando López, Syuzanna R Harutyunyan, Adriaan J Minnaard, Ben L Feringa.   

Abstract

A highly enantioselective (up to 96% ee) conjugate addition of Grignard reagents, in particular, MeMgBr, to alpha,beta-unsaturated thioesters is provided as well as its application to a diastereo- and enantioselective iterative route to syn- and anti-1,3-dimethyl arrays and deoxypropionate subunits. The versatility of the method is illustrated in the synthesis of (-)-lardolure, a multimethyl-branched insect natural pheromone.

Entities:  

Year:  2005        PMID： 16011337     DOI： 10.1021/ja053020f

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


  18 in total

1.  Enantioselective synthesis of boron-substituted quaternary carbons by NHC-Cu-catalyzed boronate conjugate additions to unsaturated carboxylic esters, ketones, or thioesters.

Authors:  Jeannette M O'Brien; Kang-sang Lee; Amir H Hoveyda
Journal:  J Am Chem Soc       Date:  2010-08-11       Impact factor: 15.419

2.  Asymmetric Synthesis of Deoxypropionate Derivatives via Catalytic Hydrogenolysis of Enantioenriched Z-Ketene Heterodimers.

Authors:  Shi Chen; Ahmad A Ibrahim; Mukulesh Mondal; Anthony J Magee; Adam J Cruz; Kraig A Wheeler; Nessan J Kerrigan
Journal:  Org Lett       Date:  2015-06-23       Impact factor: 6.005

3.  Nonracemic Antifolates Stereoselectively Recruit Alternate Cofactors and Overcome Resistance in S. aureus.

Authors:  Santosh Keshipeddy; Stephanie M Reeve; Amy C Anderson; Dennis L Wright
Journal:  J Am Chem Soc       Date:  2015-07-08       Impact factor: 15.419

4.  Convergent synthesis of deoxypropionates.

Authors:  Peter S Diez; Glenn C Micalizio
Journal:  Angew Chem Int Ed Engl       Date:  2012-04-05       Impact factor: 15.336

5.  Asymmetric synthesis and structure elucidation of a glycerophospholipid from Mycobacterium tuberculosis.

Authors:  Bjorn Ter Horst; Chetan Seshadri; Lindsay Sweet; David C Young; Ben L Feringa; D Branch Moody; Adriaan J Minnaard
Journal:  J Lipid Res       Date:  2009-11-05       Impact factor: 5.922

6.  Stereoselective Synthesis of Baulamycin A.

Authors:  Jonathan R Thielman; David H Sherman; Robert M Williams
Journal:  J Org Chem       Date:  2020-02-07       Impact factor: 4.354

7.  Biologically active Phytophthora mating hormone prepared by catalytic asymmetric total synthesis.

Authors:  Syuzanna R Harutyunyan; Zhijian Zhao; Tim den Hartog; Klaas Bouwmeester; Adriaan J Minnaard; Ben L Feringa; Francine Govers
Journal:  Proc Natl Acad Sci U S A       Date:  2008-06-16       Impact factor: 11.205

Review 8.  Chemical Synthesis of Cell Wall Constituents of Mycobacterium tuberculosis.

Authors:  Mira Holzheimer; Jeffrey Buter; Adriaan J Minnaard
Journal:  Chem Rev       Date:  2021-06-30       Impact factor: 60.622

9.  CD1b Tetramers Identify T Cells that Recognize Natural and Synthetic Diacylated Sulfoglycolipids from Mycobacterium tuberculosis.

Authors:  Charlotte A James; Krystle K Q Yu; Martine Gilleron; Jacques Prandi; Vijayendar R Yedulla; Zuzanna Z Moleda; Eleonora Diamanti; Momin Khan; Varinder K Aggarwal; Josephine F Reijneveld; Peter Reinink; Stefanie Lenz; Ryan O Emerson; Thomas J Scriba; Michael N T Souter; Dale I Godfrey; Daniel G Pellicci; D Branch Moody; Adriaan J Minnaard; Chetan Seshadri; Ildiko Van Rhijn
Journal:  Cell Chem Biol       Date:  2018-02-01       Impact factor: 8.116

10.  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
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