An Efficient Synthesis of [2.2.1] Heterobicyclic Pyroglutamates

作者:Tekkam Srinivas; Johnson Joseph L; Jonnalagadda Subash C; Mereddy Venkatram R*
来源:Journal of Heterocyclic Chemistry, 2013, 50(4): 969-972.
DOI:10.1002/jhet.1097

摘要

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, RhCl3-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.

  • 出版日期2013-7