Reactions of indole derivatives with oxiranes and aziridines on silica. Synthesis of β-carbolin-1-one mimic of pancratistatin

Tomas Hudlicky, Uwe Rinner, Kevin J. Finn, Ion Ghiviriga

Research output: Contribution to journalArticle

66 Citations (Scopus)

Abstract

(Chemical Equation Presented) Indole and several indoles functionalized at C-2 were condensed with oxiranes, vinyloxiranes, aziridines, and vinylaziridines in the solid state on the surface of silica. The yields of these reactions were compared to those obtained from Lewis acid-catalyzed ring-opening reactions performed in solution and found to be superior in each case. The solid-phase aziridine opening constituted a key step in the synthesis of the β-carbolin-1-one mimic of pancratistatin. Methyl 2-indolecarboxylate was found to react on the silica gel surface with N-tosylvinylaziridine in 68% yield. A nine-step synthesis of the pancratistatin mimic has been attained. The additional key transformation in this synthesis involved silica gel-catalyzed opening of an epoxide and hydrolysis of an acetonide. Detailed experimental procedures and full characterization are reported for all new compounds.

Original languageEnglish
Pages (from-to)3490-3499
Number of pages10
JournalJournal of Organic Chemistry
Volume70
Issue number9
DOIs
Publication statusPublished - Apr 29 2005

ASJC Scopus subject areas

  • Organic Chemistry

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