A facilitated cyclic ether formation and its potential application in solid-phase peptide and organic synthesis

Daxian Shan, Ailian Zheng, C. Eric Ballard, Wei Wang, Ronald T. Borchardt, Binghe Wang

Research output: Contribution to journalArticlepeer-review

4 Scopus citations

Abstract

A 'trimethyl lock' system has been known to facilitate lactonization reactions through what has been termed a stereopopulation control 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.

Original languageEnglish (US)
Pages (from-to)238-244
Number of pages7
JournalChemical and Pharmaceutical Bulletin
Volume48
Issue number2
DOIs
StatePublished - Feb 2000
Externally publishedYes

Keywords

  • 'Trimethyl lock'
  • Cyclization
  • Fluoride
  • Hydroquinone
  • Linker
  • Quinone

ASJC Scopus subject areas

  • Chemistry(all)
  • Drug Discovery

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