Literature DB >> 20161213

Strategic use of nickel(0)-catalyzed enyne-epoxide reductive coupling towards the synthesis of (-)-cyatha-3,12-diene.

Brian A Sparling1, Graham L Simpson, Timothy F Jamison.   

Abstract

Various situations are explored in which the nickel(0)-catalyzed enyne-epoxide reductive coupling was utilized to access key intermediates towards the total synthesis of (-)-cyatha-3,12-diene (1). Enantioenriched 3,5-dien-1-ols with a variety of functionality were obtained in a straightforward manner from easily accessible 1,3-enynes and terminal epoxides.

Entities:  

Year:  2009        PMID： 20161213      PMCID： PMC2716032          DOI： 10.1016/j.tet.2008.11.086

Source DB:  PubMed          Journal:  Tetrahedron        ISSN： 0040-4020            Impact factor:   2.457


  25 in total

1.  The Type 2 Intramolecular Diels-Alder Reaction: Synthesis and Chemistry of Bridgehead Alkenes.

Authors:  Brian R. Bear; Steven M. Sparks; Kenneth J. Shea
Journal:  Angew Chem Int Ed Engl       Date:  2001-03-02       Impact factor: 15.336

2.  Asymmetric catalytic coupling of organoboranes, alkynes, and imines with a removable (trialkylsilyloxy)ethyl group--direct access to enantiomerically pure primary allylic amines.

Authors:  Sejal J Patel; Timothy F Jamison
Journal:  Angew Chem Int Ed Engl       Date:  2004-07-26       Impact factor: 15.336

3.  Total synthesis of (+)-allocyathin B2.

Authors:  Barry M Trost; Li Dong; Gretchen M Schroeder
Journal:  J Am Chem Soc       Date:  2005-03-09       Impact factor: 15.419

Review 4.  Recent advances in natural product synthesis by using intramolecular Diels-Alder reactions.

Authors:  Ken-Ichi Takao; Ryosuke Munakata; Kin-ichi Tadano
Journal:  Chem Rev       Date:  2005-12       Impact factor: 60.622

5.  Highly selective catalytic intermolecular reductive coupling of alkynes and aldehydes

Authors: 
Journal:  Org Lett       Date:  2000-12-28       Impact factor: 6.005

6.  Total syntheses of amphidinolides T1 and T4 via catalytic, stereoselective, reductive macrocyclizations.

Authors:  Elizabeth A Colby; Karen C O'Brien; Timothy F Jamison
Journal:  J Am Chem Soc       Date:  2005-03-30       Impact factor: 15.419

7.  Catalytic asymmetric reductive coupling of alkynes and aldehydes: enantioselective synthesis of allylic alcohols and alpha-hydroxy ketones.

Authors:  Karen M Miller; Wei-Sheng Huang; Timothy F Jamison
Journal:  J Am Chem Soc       Date:  2003-03-26       Impact factor: 15.419

8.  Nickeladihydrofuran. Key intermediate for nickel-catalyzed reaction of alkyne and aldehyde.

Authors:  Sensuke Ogoshi; Tomoya Arai; Masato Ohashi; Hideo Kurosawa
Journal:  Chem Commun (Camb)       Date:  2008-01-21       Impact factor: 6.222

9.  Alkene-directed, nickel-catalyzed alkyne coupling reactions.

Authors:  Karen M Miller; Torsak Luanphaisarnnont; Carmela Molinaro; Timothy F Jamison
Journal:  J Am Chem Soc       Date:  2004-04-07       Impact factor: 15.419

10.  Total synthesis of pumiliotoxins 209F and 251D via late-stage, nickel-catalyzed epoxide-alkyne reductive cyclization.

Authors:  Katrina S Woodin; Timothy F Jamison
Journal:  J Org Chem       Date:  2007-08-14       Impact factor: 4.354
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  3 in total

1.  Ni(II) salts and 2-propanol effect catalytic reductive coupling of epoxides and alkynes.

Authors:  Matthew G Beaver; Timothy F Jamison
Journal:  Org Lett       Date:  2011-06-30       Impact factor: 6.005

2.  A tetraene aldehyde as the major sex pheromone component of the promethea moth (Callosamia promethea (Drury)).

Authors:  Rafael Gago; Jeremy D Allison; J Steven McElfresh; Kenneth F Haynes; Jessica McKenney; Angel Guerrero; Jocelyn G Millar
Journal:  J Chem Ecol       Date:  2013-10-03       Impact factor: 2.626

3.  Origins of regioselectivity and alkene-directing effects in nickel-catalyzed reductive couplings of alkynes and aldehydes.

Authors:  Peng Liu; Patrick McCarren; Paul Ha-Yeon Cheong; Timothy F Jamison; K N Houk
Journal:  J Am Chem Soc       Date:  2010-02-17       Impact factor: 15.419
  3 in total

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