Bicyclic oxygen heterocycles from γ,δ-unsaturated alcohols: Synthetic targets inspired by blepharocalyxin D

Adam J. Bunt, Christopher D. Bailey, Benjamin D. Cons, Sophie J. Edwards, Jon D. Elsworth, Tshepo Pheko, Christine L. Willis

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Abstract

trans-2,8-Dioxabicyclodecanes were prepared in high yield with the creation of up to three stereocenters in a single pot by the acid-mediated reaction of γ,δ-unsaturated alcohols with aldehydes (see scheme, Bn=benzyl). This versatile reaction enables the stereoselective introduction of substituents at the C3, C4, C7, and C9 positions of the bicyclic framework.

Original languageEnglish
Pages (from-to)3901-3904
Number of pages4
JournalAngewandte Chemie - International Edition
Volume51
Issue number16
DOIs
Publication statusPublished - Apr 16 2012

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All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)

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