Hydroxyl-Substituted Ladder Polyethers via Selective Tandem Epoxidation/Cyclization Sequence
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Jamison_Hydroxyl-substituted.pdf
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Author(s)
Czabaniuk, Lara Christine
Jamison, Timothy F
Date Issued
February 2015
Journal
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
Abstract
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.
MIT Department
Massachusetts Institute of Technology. Department of Chemistry
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DOI of Published Version
https://doi.org/10.1021/ol503400j
