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Hydroxyl-Substituted Ladder Polyethers via Selective Tandem Epoxidation/Cyclization Sequence
- Czabaniuk, Lara C., Jamison, Timothy F.
- Organic letters 2015 v.17 no.4 pp. 774-777
- chemical structure, diastereoselectivity, epoxidation reactions, organic compounds, regioselectivity, titanium, yessotoxin
- A new and highly selective method for the synthesis of hydroxyl-substituted tetrahydropyrans is described. This method utilizes titanium(IV) isopropoxide and diethyl tartrate to perform a diastereoselective epoxidation followed by in situ epoxide activation and highly selective endo-cyclization to form the desired tetrahydropyran ring. The HIJ ring fragment of the marine ladder polyether yessotoxin was synthesized using this two-stage tactic that proceeds with high efficiency and excellent regioselectivity.