Evaluation of 'east-to-west' ether-forming strategies for the total synthesis of maoecrystal v

Kiel E. Lazarski, Berkcan Akpinar, Regan James Thomson*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

21 Scopus citations

Abstract

Model systems that evaluated different approaches to construct the central ether ring of maoecrystal V are described. Our first model systems attempted the ether formation using C-H functionalization reactions, which led to interesting rearrangements but none of the desired ether product. An intramolecular conjugate addition strategy was then explored that successfully formed the targeted C-O bond but resulted in the undesired stereochemistry.

Original languageEnglish (US)
Pages (from-to)635-637
Number of pages3
JournalTetrahedron Letters
Volume54
Issue number7
DOIs
StatePublished - Feb 13 2013

Keywords

  • Etherification
  • Maoecrystal V
  • Oxy-1,4-addition

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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