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A Facilitated Cyclic Ether Formation and Its Potential Application in Solid-Phase Peptide and Organic Synthesis
Shan, Daxian Zheng, Ailian Ballard, C. Eric Wang, Wei Borchardt, Ronald T. Wang, Binghe
Shan, Daxian
Zheng, Ailian
Ballard, C. Eric
Wang, Wei
Borchardt, Ronald T.
Wang, Binghe
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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.
Description
Date
2000
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Publisher
The Pharmaceutical Society of Japan
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Research Projects
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Keywords
"Trimethyl lock", Cyclization, Linker, Fluoride, Quinone, Hydroquinone
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