Literature DB >> 11674045

Acid-Mediated Conversion of Methylene-Interrupted Bisepoxides to Tetrahydrofurans: A Biomimetic Transformation.

Robert J. Capon1, Russell A. Barrow.   

Abstract

The acid-mediated transformation of syn and anti methylene interrupted cis,cis and cis,trans bisepoxides to tetrahydrofurans is high yielding, and demonstrates both regioselectivity and stereoselectivity. Trans,trans methylene interrupted bisepoxides do not yield tetrahydrofurans under the same conditions.

Entities:  

Year:  1998        PMID： 11674045     DOI： 10.1021/jo971147k

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  4 in total

1.  Recent Advances in the Stereoselective Synthesis of Tetrahydrofurans.

Authors:  John P Wolfe; Michael B Hay
Journal:  Tetrahedron       Date:  2007-01-08       Impact factor: 2.457

2.  An expeditious total synthesis of both diastereoisomeric lipid dihydroxytetrahydrofurans from Notheia anomala.

Authors:  Sudeshna Roy; Christopher D Spilling
Journal:  Org Lett       Date:  2012-04-16       Impact factor: 6.005

Review 3.  Epoxide-opening cascades in the synthesis of polycyclic polyether natural products.

Authors:  Ivan Vilotijevic; Timothy F Jamison
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

4.  Synthesis of triazolo-fused benzoxazepines and benzoxazepinones via Passerini reactions followed by 1,3-dipolar cycloadditions.

Authors:  Fabio De Moliner; Martina Bigatti; Chiara De Rosa; Luca Banfi; Renata Riva; Andrea Basso
Journal:  Mol Divers       Date:  2014-06-04       Impact factor: 2.943
  4 in total

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