| dc.contributor.author | Czabaniuk, Lara Christine | |
| dc.contributor.author | Jamison, Timothy F | |
| dc.date.accessioned | 2017-07-05T17:38:29Z | |
| dc.date.available | 2017-07-05T17:38:29Z | |
| dc.date.issued | 2015-02 | |
| dc.date.submitted | 2014-11 | |
| dc.identifier.issn | 1523-7060 | |
| dc.identifier.issn | 1523-7052 | |
| dc.identifier.uri | http://hdl.handle.net/1721.1/110467 | |
| dc.description.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. | en_US |
| dc.description.sponsorship | National Institute of General Medical Sciences (U.S.) (GM72566) | en_US |
| dc.description.sponsorship | National Science Foundation (U.S.) (CHE-0234877) | en_US |
| dc.description.sponsorship | National Science Foundation (U.S.) (CHE-9808061) | en_US |
| dc.language.iso | en_US | |
| dc.publisher | American Chemical Society (ACS) | en_US |
| dc.relation.isversionof | http://dx.doi.org/10.1021/ol503400j | en_US |
| dc.rights | Article is made available in accordance with the publisher's policy and may be subject to US copyright law. Please refer to the publisher's site for terms of use. | en_US |
| dc.source | PMC | en_US |
| dc.title | Hydroxyl-Substituted Ladder Polyethers via Selective Tandem Epoxidation/Cyclization Sequence | en_US |
| dc.type | Article | en_US |
| dc.identifier.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 | en_US |
| dc.contributor.department | Massachusetts Institute of Technology. Department of Chemistry | en_US |
| dc.contributor.mitauthor | Czabaniuk, Lara Christine | |
| dc.contributor.mitauthor | Jamison, Timothy F | |
| dc.relation.journal | Organic Letters | en_US |
| dc.eprint.version | Author's final manuscript | en_US |
| dc.type.uri | http://purl.org/eprint/type/JournalArticle | en_US |
| eprint.status | http://purl.org/eprint/status/PeerReviewed | en_US |
| dspace.orderedauthors | Czabaniuk, Lara C.; Jamison, Timothy F. | en_US |
| dspace.embargo.terms | N | en_US |
| dc.identifier.orcid | https://orcid.org/0000-0002-8601-7799 | |
| mit.license | PUBLISHER_POLICY | en_US |
