Bicyclic oxygen heterocycles from γ,δ-unsaturated alcohols Synthetic Targets: Inspired by Blepharocalyxin D†: 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

Research output: Contribution to journalArticle (Academic Journal)peer-review

48 Citations (Scopus)

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)3901-4
Number of pages4
JournalAngewandte Chemie - International Edition
Volume51
Issue number16
DOIs
Publication statusPublished - Apr 2012

Structured keywords

  • BCS and TECS CDTs

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