An efficient synthesis of [2.2.1] heterobicyclic pyroglutamates

Srinivas Tekkam, Joseph L. Johnson, Subash C. Jonnalagadda, Venkatram R. Mereddy

Research output: Contribution to journalArticlepeer-review

4 Scopus citations

Abstract

A novel methodology for the efficient synthesis of [2.2.1] heterobicyclic pyroglutamates has been described. The key synthetic steps involve alkylation of amino acid-derived iminoesters with Baylis-Hillman bromide, RhCl 3-catalyzed exocyclic olefin isomerization, diastereoselective dihydroxylation, and regioselective lactonization. All the compounds were evaluated for their cytotoxicity using multiple myeloma cancer cell lines RPMI 8226.

Original languageEnglish (US)
Pages (from-to)969-972
Number of pages4
JournalJournal of Heterocyclic Chemistry
Volume50
Issue number4
DOIs
StatePublished - Jul 1 2013

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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