dc.contributor.author | Shan, Daxian | |
dc.contributor.author | Zheng, Ailian | |
dc.contributor.author | Ballard, C. Eric | |
dc.contributor.author | Wang, Wei | |
dc.contributor.author | Borchardt, Ronald T. | |
dc.contributor.author | Wang, Binghe | |
dc.date.accessioned | 2015-05-13T15:54:04Z | |
dc.date.available | 2015-05-13T15:54:04Z | |
dc.date.issued | 2000 | |
dc.identifier.citation | Shan et al. "A Facilitated Cyclic Ether Formation and Its Potential Application in Solid-Phase Peptide and Organic Synthesis." Chemical and Pharmaceutical Bulletin Vol. 48 (2000) No. 2 P 238-244. http://doi.org/10.1248/cpb.48.238 | en_US |
dc.identifier.uri | http://hdl.handle.net/1808/17746 | |
dc.description.abstract | A "trimethyl lock" system has been known to facilitate lactonization reactions through what has been termed a stereopopulation contorl mechanism. We have found that a similar trimethyl lock system can also facilitate cyclic ether formation with the concomitant release of a carboxylic acid in the presence of anhydrous tetrabutylammonium fluoride. To study this base-mediated trimethyl lock-facilitated cyclic ether formation, we synthesized fifteen model compounds. All model compounds underwent base-mediated cyclic ether formation in high yields at 0°C to room temperature (r.t.) with the concomitant release of the attached carboxylate. Such a system potentially could be used for the development of a two-dimensional linker for solid phase peptide and organic synthesis. | en_US |
dc.publisher | The Pharmaceutical Society of Japan | en_US |
dc.subject | "Trimethyl lock" | en_US |
dc.subject | Cyclization | en_US |
dc.subject | Linker | en_US |
dc.subject | Fluoride | en_US |
dc.subject | Quinone | en_US |
dc.subject | Hydroquinone | en_US |
dc.title | A Facilitated Cyclic Ether Formation and Its Potential Application in Solid-Phase Peptide and Organic Synthesis | en_US |
dc.type | Article | |
kusw.kuauthor | Borchardt, Ronald T. | |
kusw.kudepartment | Department of Pharmaceutical Chemistry | en_US |
dc.identifier.doi | 10.1248/cpb.48.238 | |
dc.identifier.orcid | https://orcid.org/0000-0002-2200-5270 | |
kusw.oaversion | Scholarly/refereed, publisher version | |
kusw.oapolicy | This item does not meet KU Open Access policy criteria. | |
dc.rights.accessrights | openAccess | |