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

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

Research output: Contribution to journalArticle

12 Citations (Scopus)

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
StatePublished - Nov 21 2009

Fingerprint

Dioxanes
Peroxides
Acids
Alkynes
Propionates
Alkylation
Biological Products
1,4-dioxane

Keywords

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

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

Asymmetric synthesis of 1,2-dioxanes : approaches to the peroxyplakoric acids. / Xu, Chunping; Schwartz, Chris; Raible, Joseph; Dussault, Patrick H.

In: Tetrahedron, Vol. 65, No. 47, 21.11.2009, p. 9680-9685.

Research output: Contribution to journalArticle

Xu, Chunping ; Schwartz, Chris ; Raible, Joseph ; Dussault, Patrick H. / Asymmetric synthesis of 1,2-dioxanes : approaches to the peroxyplakoric acids. In: Tetrahedron. 2009 ; Vol. 65, No. 47. pp. 9680-9685.
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