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

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

doi:10.1016/j.tet.2009.09.068

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

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

Chemistry

Research output: Contribution to journal › Article › peer-review

19 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 language	English (US)
Pages (from-to)	9680-9685
Number of pages	6
Journal	Tetrahedron
Volume	65
Issue number	47
DOIs	https://doi.org/10.1016/j.tet.2009.09.068
State	Published - Nov 21 2009

Keywords

1,2-Dioxane
Intramolecular alkylation
Peroxide
Peroxyplakoric

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tet.2009.09.068

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AU - Dussault, Patrick H.

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AB - 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.

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KW - Intramolecular alkylation

KW - Peroxide

KW - Peroxyplakoric

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

Abstract

Keywords

ASJC Scopus subject areas

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