A Facilitated Cyclic Ether Formation and Its Potential Application in Solid-Phase Peptide and Organic Synthesis

View/ Open
Issue Date
2000Author
Shan, Daxian
Zheng, Ailian
Ballard, C. Eric
Wang, Wei
Borchardt, Ronald T.
Wang, Binghe
Publisher
The Pharmaceutical Society of Japan
Type
Article
Article Version
Scholarly/refereed, publisher version
Metadata
Show full item recordAbstract
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.
Collections
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
Items in KU ScholarWorks are protected by copyright, with all rights reserved, unless otherwise indicated.
We want to hear from you! Please share your stories about how Open Access to this item benefits YOU.