Literature DB >> 14535734

Stereoselective construction of cis-2,6-disubstituted tetrahydropyrans via the reductive etherification of delta-trialkylsilyloxy substituted ketones: total synthesis of (-)-centrolobine.

P Andrew Evans1, Jian Cui, Santosh J Gharpure.   

Abstract

[reaction: see text] The stereoselective intramolecular reductive etherification of delta-trialkylsilyloxy substituted ketones with catalytic bismuth tribromide and triethylsilane provides a convenient method for the construction of cis-2,6-disubstituted tetrahydropyrans. This method was highlighted in the key step of an expeditious total synthesis of the antibiotic, (-)-centrolobine.

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Year:  2003        PMID： 14535734      PMCID： PMC1821343          DOI： 10.1021/ol035438t

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


  5 in total

1.  Constituents of Brosimum potabile.

Authors:  A F Alcântara; M R Souza; D Piló-Veloso
Journal:  Fitoterapia       Date:  2000-09       Impact factor: 2.882

2.  Synthesis of (-)-centrolobine by Prins cyclizations that avoid racemization.

Authors:  Shinji Marumoto; James J Jaber; Justin P Vitale; Scott D Rychnovsky
Journal:  Org Lett       Date:  2002-10-31       Impact factor: 6.005

3.  Recent developments in olefin cross-metathesis.

Authors:  Stephen J Connon; Siegfried Blechert
Journal:  Angew Chem Int Ed Engl       Date:  2003-04-29       Impact factor: 15.336

4.  First enantioselective total synthesis of (-)-Centrolobine.

Authors:  Françoise Colobert; Renaud Des Mazery; Guy Solladié; M Carmen Carreño
Journal:  Org Lett       Date:  2002-05-16       Impact factor: 6.005

5.  Stereoselective construction of cyclic ethers using a tandem two-component etherification: elucidation of the role of bismuth tribromide.

Authors:  P Andrew Evans; Jian Cui; Santosh J Gharpure; Robert J Hinkle
Journal:  J Am Chem Soc       Date:  2003-09-24       Impact factor: 15.419
  5 in total
  6 in total

1.  Bi(OTf)3-, TfOH-, and TMSOTf-mediated, one-pot epoxide rearrangement, addition, and intramolecular silyl-modified Sakurai (ISMS) cascade toward dihydropyrans: comparison of catalysts and role of Bi(OTf)3.

Authors:  R Frederick Lambert; Robert J Hinkle; Stephen E Ammann; Yajing Lian; Jia Liu; Shane E Lewis; Robert D Pike
Journal:  J Org Chem       Date:  2011-10-25       Impact factor: 4.354

2.  Stereoselective construction of cis-2,6-disubstituted tetrahydropyrans via an intramolecular bismuth-mediated oxa-conjugate addition reaction.

Authors:  P Andrew Evans; William J Andrews
Journal:  Tetrahedron Lett       Date:  2005-08-22       Impact factor: 2.415

3.  Total synthesis of brevenal.

Authors:  Yuan Zhang; John Rohanna; Jie Zhou; Karthik Iyer; Jon D Rainier
Journal:  J Am Chem Soc       Date:  2011-02-15       Impact factor: 15.419

4.  Stereoselective synthesis of cyclic ethers via the palladium-catalyzed intramolecular addition of alcohols to phosphono allylic carbonates.

Authors:  Anyu He; Nongnuch Sutivisedsak; Christopher D Spilling
Journal:  Org Lett       Date:  2009-07-16       Impact factor: 6.005

5.  Enantioselective total synthesis of the potent antitumor agent (-)-mucocin using a temporary silicon-tethered ring-closing metathesis cross-coupling reaction.

Authors:  P Andrew Evans; Jian Cui; Santosh J Gharpure; Alexei Polosukhin; Hai-Ren Zhang
Journal:  J Am Chem Soc       Date:  2003-12-03       Impact factor: 15.419

6.  Total synthesis of annonaceous acetogenins belonging to the non-adjacent bis-THF and non-adjacent THF-THP sub-classes.

Authors:  Ian B Spurr; Richard C D Brown
Journal:  Molecules       Date:  2010-01-21       Impact factor: 4.411
  6 in total

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