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Beilstein J Org Chem. 2015 Jun 15;11:1017-22. doi: 10.3762/bjoc.11.114. eCollection 2015.

Novel carbocationic rearrangements of 1-styrylpropargyl alcohols.

Beilstein journal of organic chemistry

Christine Basmadjian, Fan Zhang, Laurent Désaubry

Affiliations

  1. Laboratory of Therapeutic Innovation (UMR 7200), University of Strasbourg - CNRS, Faculty of Pharmacy, 67401 Illkirch, France.

PMID: 26199656 PMCID: PMC4505300 DOI: 10.3762/bjoc.11.114

Abstract

The dehydration and subsequent cyclization reactions of 1-styrylpropargyl alcohols was examined. In the course of these studies, numerous scaffolds were synthesized, including a furan, a cyclopentenone, an acyclic enone and even a naphthalenone. The diversity of these structural motifs lies in novel cascades of reactions originating from a common carbocationic manifold.

Keywords: carbocationic rearrangement; cyclopentenones; furans; propargyl alcohols

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