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) |
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Pages (from-to) | 9680-9685 |
Number of pages | 6 |
Journal | Tetrahedron |
Volume | 65 |
Issue number | 47 |
DOIs | |
State | Published - Nov 21 2009 |
Keywords
- 1,2-Dioxane
- Intramolecular alkylation
- Peroxide
- Peroxyplakoric
ASJC Scopus subject areas
- Biochemistry
- Drug Discovery
- Organic Chemistry