Synthesis of functionalized pyroglutamic acids, part 1: The synthetic utility of N-acylindole and the ugi reaction with a chiral levulinic acid

Matthew J. Buller, Cynthia B. Gilley, Brian Nguyen, Lisa Olshansky, Breena Fraga, Yoshihisa Kobayashi

Research output: Contribution to journalArticlepeer-review

Abstract

A variety of pyroglutamic acid derivatives are readily synthesized via N-acylindole intermediates obtained by the Ugi reaction. For the preparation of functionalized pyroglutamic acid derivatives, the diastereoselectivity of the Ugi 4-center 3-component condensation reaction with a chiral γ-keto acid and convertible isocyanide is described.

Original languageEnglish (US)
Pages (from-to)2244-2248
Number of pages5
JournalSynlett
Issue number15
DOIs
StatePublished - Sep 15 2008
Externally publishedYes

Keywords

  • Convertible isocyanide
  • Diastereoselectivity
  • Pyroglutamic acid
  • Ugi reaction
  • β-lactone

ASJC Scopus subject areas

  • Organic Chemistry

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