Hydroxyl-Substituted Ladder Polyethers via Selective Tandem Epoxidation/Cyclization Sequence
Author(s)
Czabaniuk, Lara Christine; Jamison, Timothy F
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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.
Date issued
2015-02Department
Massachusetts Institute of Technology. Department of ChemistryJournal
Organic Letters
Publisher
American Chemical Society (ACS)
Citation
Czabaniuk, Lara C. and Jamison, Timothy F. "Hydroxyl-Substituted Ladder Polyethers via Selective Tandem Epoxidation/Cyclization Sequence." Organic Letters 17, 4 (February 2014): 774–777 © 2015 American Chemical Society
Version: Author's final manuscript
ISSN
1523-7060
1523-7052