Asymmetric synthesis of 1,2-dioxanes: approaches to the peroxyplakoric acids

Chunping Xu, Chris Schwartz, Joseph Raible, Patrick H. Dussault

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13 Scopus citations

Abstract

The stereospecific intramolecular alkylation of a hydroperoxyacetal provides the basis for the first asymmetric synthesis of the dioxane propionate core of the peroxyplakorates. Chemoselective hydrometallation of an alkyne in the presence of a peroxide is used to introduce a synthon for the polyunsaturated side chains of the peroxyplakorates. The route suggests a general solution for the 1,2-dioxane unit in many peroxide natural products.

Original languageEnglish (US)
Pages (from-to)9680-9685
Number of pages6
JournalTetrahedron
Volume65
Issue number47
DOIs
Publication statusPublished - Nov 21 2009

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Keywords

  • 1,2-Dioxane
  • Intramolecular alkylation
  • Peroxide
  • Peroxyplakoric

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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