Solid-Phase Synthesis of an Isoxazolinopyrrole Library

Sung Hee Hwang, Marilyn M. Olmstead, Mark J. Kurth

Research output: Contribution to journalArticle

20 Scopus citations

Abstract

A four-step solid-phase synthesis of isoxazolinopyrroles 8 that employs an acid-labile 2-(4-formyl-3-methoxyphenoxy)ethyl polystyrene HL resin 1 is reported. Resin-bound vinyl sulfone 5 is obtained by DIC coupling with acid 4, which was in turn synthesized in solution phase by a regioselective nitrile oxide 1,3-dipolar cycloaddition. The resin-bound pyrrole 7 was synthesized on solid phase by pyrrole annulation with various isocyano derivatives and potassium t-butoxide in which the sulfone α-anion generated by Michael addition gives the desired pyrrole through internal condensation followed by a sigmatropic [1,5]-hydrogen shift. The resulting isoxazolinopyrroles 8 were released from resin 7 by 10% TFA in moderate to excellent overall yields from 2-(4-formyl-3-methoxyphenoxy)ethyl polystyrene HL resin 1.

Original languageEnglish (US)
Pages (from-to)142-148
Number of pages7
JournalJournal of Combinatorial Chemistry
Volume6
Issue number1
DOIs
StatePublished - Jan 2004

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ASJC Scopus subject areas

  • Drug Discovery
  • Organic Chemistry
  • Chemistry(all)
  • Discrete Mathematics and Combinatorics

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