Literature DB >> 16909163

Stereoselective synthesis of the C(1)-C(13) segment of dolabelide B.

Gary E Keck1, Mark D McLaws.   

Abstract

The efficient construction of the C(1)-C(13) segment of dolabelide B is described. A key element of the synthesis entails BITIP catalyzed asymmetric methallylation to establish the C(7) stereocenter, which was then used to direct the stereoselective installation of the C(9) and C(11) centers through Evans reduction and 1,5-anti aldol condensation, respectively.

Entities:  

Year:  2005        PMID： 16909163      PMCID： PMC1540402          DOI： 10.1016/j.tetlet.2005.04.146

Source DB:  PubMed          Journal:  Tetrahedron Lett        ISSN： 0040-4039            Impact factor:   2.415


  8 in total

1.  The first directed reduction of beta-alkoxy ketones to anti-1,3-diol monoethers: identification of spectator and director alkoxy groups.

Authors:  G E Keck; C A Wager
Journal:  Org Lett       Date:  2000-07-27       Impact factor: 6.005

2.  Asymmetric Total Synthesis of Rhizoxin D Financial support has been provided by the National Institutes of Health (through grant GM-28961) and by Pfizer, Inc.

Authors:  Gary E. Keck; Carrie A. Wager; Travis T. Wager; Kenneth A. Savin; Jonathan A. Covel; Mark D. McLaws; Dhileep Krishnamurthy; Victor J. Cee
Journal:  Angew Chem Int Ed Engl       Date:  2001-01-05       Impact factor: 15.336

3.  Diastereoselective synthesis of protected syn 1,3-diols: preparation of the C16-C24 portion of Dolabelides.

Authors:  Laurence Grimaud; Romain de Mesmay; Joëlle Prunet
Journal:  Org Lett       Date:  2002-02-07       Impact factor: 6.005

4.  Total synthesis of the immunosupressant (-)-pironetin (PA48153C).

Authors:  G E Keck; C E Knutson; S A Wiles
Journal:  Org Lett       Date:  2001-03-08       Impact factor: 6.005

5.  Reduction of beta-hydroxyketones by SmI2/H2O/Et3N.

Authors:  Todd A Davis; Pramod R Chopade; Göran Hilmersson; Robert A Flowers
Journal:  Org Lett       Date:  2005-01-06       Impact factor: 6.005

6.  Directed reduction of beta-amino ketones to syn or anti 1,3-amino alcohol derivatives.

Authors:  Gary E Keck; Anh P Truong
Journal:  Org Lett       Date:  2002-09-05       Impact factor: 6.005

7.  Approach to the synthesis of dolabelides A and B: fragment synthesis by tandem silylformylation-crotylsilylation.

Authors:  Darby R Schmidt; Peter K Park; James L Leighton
Journal:  Org Lett       Date:  2003-09-18       Impact factor: 6.005

8.  Solvent-dependent diastereoselectivities in reductions of beta-hydroxyketones by SmI2.

Authors:  Pramod R Chopade; Todd A Davis; Edamana Prasad; Robert A Flowers
Journal:  Org Lett       Date:  2004-08-05       Impact factor: 6.005
  8 in total
  5 in total

1.  Super silyl stereo-directing groups for complete 1,5-syn and -anti stereoselectivities in the aldol reactions of beta-siloxy methyl ketones with aldehydes.

Authors:  Yousuke Yamaoka; Hisashi Yamamoto
Journal:  J Am Chem Soc       Date:  2010-04-21       Impact factor: 15.419

2.  Total synthesis of dolabelide D.

Authors:  Peter K Park; Steven J O'Malley; Darby R Schmidt; James L Leighton
Journal:  J Am Chem Soc       Date:  2006-03-08       Impact factor: 15.419

3.  Total synthesis of dolabelide C: a phosphate-mediated approach.

Authors:  Paul R Hanson; Rambabu Chegondi; John Nguyen; Christopher D Thomas; Joshua D Waetzig; Alan Whitehead
Journal:  J Org Chem       Date:  2011-04-29       Impact factor: 4.354

4.  A multifaceted phosphate tether: application to the C1-C14 subunit of dolabelides A-D.

Authors:  Joshua D Waetzig; Paul R Hanson
Journal:  Org Lett       Date:  2007-12-07       Impact factor: 6.005

5.  A multifaceted phosphate tether: application to the C15-C30 subunit of dolabelides A-D.

Authors:  Alan Whitehead; Joshua D Waetzig; Christopher D Thomas; Paul R Hanson
Journal:  Org Lett       Date:  2008-03-07       Impact factor: 6.005
  5 in total

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